Water → HCID 86738622, compound

HRID 2198513Notes

Reaction equation

HRID 2198513 reaction equation
C(OP([CH:9]([Cl:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=O)OCC)C.C[O-].[Na+].[CH3:21][C:22]1([CH3:30])[C@@H:24]([CH:25]=O)[C@@H:23]1[C:27](=[O:29])[CH3:28].O>O1CCCC1.CO>[CH3:21][C:22]1([CH3:30])[C@@H:23]([C:27](=[O:29])[CH3:28])[C@@H:24]1[CH:25]=[C:9]([Cl:17])[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 12881548Diethyl [chloro(4-chlorophenyl)methyl]phosphonateHCID 53675424trans-3,3-Dimethyl-2-acetyl-cyclopropanecarbaldehyde

Product 1

HCID 86738622HCID 86738622, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 23.7 g (0.08 mol) of α-chloro-(4-chlorobenzyl)-phosphonic acid diethyl ester in 40 ml of tetrahydrofuran was added dropwise to a solution of 17.8 g (0.084 mol) of sodium methylate in methanol and 160 ml of tetrahydrofuran at 0°-10° C. and the mixture was subsequently stirred at 0°-10° C. for 1 hour. 11.2 g (0.08 mol) of trans-3,3-dimethyl-2-acetyl-cyclopropanecarbaldehyde were then added at 10° C. and the reaction mixture was subsequently stirred for 2 hours, without further cooling, and then poured onto 800 ml of water. The aqueous solution was extracted three times with 200 ml of methylene chloride each time and the combined organic phases were dried over sodium sulphate and evaporated in vacuo. 19.7 g (87% of theory) of trans-3,3-dimethyl-2-(2-chloro-2-(4-chlorophenyl)-vinyl)-1-acetyl-cyclopropane were thus obtained as a yellow oil with a boiling point of 120°-128° C./0.1 mm/Hg. ##STR53##

Workup

  1. stirringthe reaction mixture was subsequently stirred for 2 hours, without further cooling
  2. extractionThe aqueous solution was extracted three times with 200 ml of methylene chloride each time
  3. dry with materialthe combined organic phases were dried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e5200433d3c146d096c03bcfaaddea13
Source dataset
uspto-grants-1982_11
Patent number
US04358409

Reaction notes

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