Acetone → 3-(4-Methoxyphenyl)-2,2-dimethylcyclopropane-1-carboxylic acid

HRID 978217Notes

Reaction equation

HRID 978217 reaction equation
CC(C)=O.[OH-:5].[Na+].Br[CH2:8][C:9](=O)[C:10]([CH3:22])([CH3:21])[CH:11](Cl)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[OH2:24]>>[CH3:21][C:10]1([CH3:22])[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]1[C:8]([OH:24])=[O:5]

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 202053461-Bromo-4-chloro-4-(4-methoxyphenyl)-3,3-dimethylbutan-2-one

Product 1

HCID 223475153-(4-Methoxyphenyl)-2,2-dimethylcyclopropane-1-carboxylic acidYield 69%

Conditions

Temperature
25 °C

Procedure

100 ml of acetone are added to a solution of 35.3 g (0.882 mol) of sodium hydroxide in 317 ml of water. Then, at 25° C., 26.5 g (0.083 mol) of 4-bromo-2,2-dimethyl-1-chloro-1-(4-methoxyphenyl)-3-butanone are added dropwise. The mixture is stirred at 25° C. for a further 12 hours, poured onto water and extracted with methylene chloride. The aqueous phase is acidified and extracted again. 12.6 g (69% of theory) of 2,2-dimethyl-3-(4-methoxyphenyl)cyclopropanecarboxylic acid of melting point 115° C. are obtained.

Workup

  1. additionpoured onto water
  2. extractionextracted with methylene chloride
  3. extractionextracted again

Sources & evidence

ORD record
ord-2fb10fdab92046158ddef63747c639f3
Source dataset
uspto-grants-1987_05
Patent number
US04663465

Reaction notes

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