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FR2353514A1 - PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES - Google Patents

PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES

Info

Publication number
FR2353514A1
FR2353514A1 FR7616759A FR7616759A FR2353514A1 FR 2353514 A1 FR2353514 A1 FR 2353514A1 FR 7616759 A FR7616759 A FR 7616759A FR 7616759 A FR7616759 A FR 7616759A FR 2353514 A1 FR2353514 A1 FR 2353514A1
Authority
FR
France
Prior art keywords
alcohol
cpds
reacted
iii
benzene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7616759A
Other languages
French (fr)
Other versions
FR2353514B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to FR7616759A priority Critical patent/FR2353514A1/en
Publication of FR2353514A1 publication Critical patent/FR2353514A1/en
Application granted granted Critical
Publication of FR2353514B1 publication Critical patent/FR2353514B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Lactones of formula (III) are reacted with a halogenating agent and then with an alcohol of formula R3OH, or the lactones (III) are reacted with the halogenating agent in the presence of the alcohol to yield cpds. of formula (II). The cpds. (II) are reacted with a base to yield 2,2-dimethyl-3-(2,2-dihalovinyl)cyclopropanecarboxylic acid derivs. (I) which are known insecticides. where X is the same or different halogen atom; one of R1 and R2 is Cl or Br and the other is -CH2COOR3 (R3 is lower alkyl), one of Y1 and Y2 is O and the other is -CH2-). The starting cpds. (III) are novel and may be prepd. from Me2C=CHCH2OH and MeC(OR3)3 via 3 steps. The halogenating agent involves SOCl2, PCl3, PBr3, HBr, HCl, SOBr2, etc. The alcohol involves MeOH, EtOH, PrOH, BuOH, etc. The base used in the 2nd step involves alkali metal alkoxide such as sodium alkoxide or t-BuOK. In the 1st steps, reaction is conducted in a solvent (e.g. petroleum ether, petroleum benzene, xylene, hexane, benzene, toluene, THF) at 0 degrees C to the b.pt. of the solvent used for 30 mins. to 20 hrs. In the 2nd step, the reaction is conducted in a solvent (e.g. alcohol, THF, Et2O, benzene, toluene) at a temp. around the b.pt. of the solvent used for 30 mins. to 10 hrs.
FR7616759A 1976-06-03 1976-06-03 PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES Granted FR2353514A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7616759A FR2353514A1 (en) 1976-06-03 1976-06-03 PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7616759A FR2353514A1 (en) 1976-06-03 1976-06-03 PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES

Publications (2)

Publication Number Publication Date
FR2353514A1 true FR2353514A1 (en) 1977-12-30
FR2353514B1 FR2353514B1 (en) 1979-06-29

Family

ID=9173936

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7616759A Granted FR2353514A1 (en) 1976-06-03 1976-06-03 PROCESS FOR THE PREPARATION OF 2,2-DIMETHYL-3- (2,2-DIHALOGENOVINYL) -CYCLOPROPANE-CARBOXYL ACID DERIVATIVES

Country Status (1)

Country Link
FR (1) FR2353514A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317298A1 (en) * 1975-07-11 1977-02-04 Ici Ltd NEW LACTONS AND THEIR PREPARATION PROCESS
FR2352786A1 (en) * 1976-05-25 1977-12-23 Cheminova As PROCESS FOR PREPARING CHRYSANTHEMIC ACID ESTERS AND THEIR APPROVALS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317298A1 (en) * 1975-07-11 1977-02-04 Ici Ltd NEW LACTONS AND THEIR PREPARATION PROCESS
FR2352786A1 (en) * 1976-05-25 1977-12-23 Cheminova As PROCESS FOR PREPARING CHRYSANTHEMIC ACID ESTERS AND THEIR APPROVALS

Also Published As

Publication number Publication date
FR2353514B1 (en) 1979-06-29

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Legal Events

Date Code Title Description
ST Notification of lapse