Hydrochloric Acid → 4-(Cyclopropylcarbonyl)benzeneacetic acid

HRID 2120382Notes

Reaction equation

HRID 2120382 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](N(OC)C)=[O:15])=[CH:9][CH:8]=1)=[O:6].[OH-:20].[K+].Cl>C(O)C>[CH:4]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]([OH:15])=[O:20])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 9857023[4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

Product 1

HCID 1937314-(Cyclopropylcarbonyl)benzeneacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add purified [4-(4-chloro-1-oxobutyl)]-N-methoxy-N-methyl-benzeneacetamide (9.4 g, 330 mmol) to a solution of potassium hydroxide (22.0 g) in ethanol (160 mL). Stir 18 hours. Pour the solution into dilute hydrochloric acid (30 mL of concentrated hydrochloric acid in 500 mL of water). Extract the solution with three 500-mL portions of ethyl acetate. Dry the combined organic phases over anhydrous magnesium sulfate and concentrate to give the title compound (6.4 g, 95%).

Workup

  1. additionAdd
  2. extractionExtract the solution with three 500-mL portions of ethyl acetate
  3. dry with materialDry the combined organic phases over anhydrous magnesium sulfate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-669d8ad8bb2349b18b7a38e250e95f8c
Source dataset
uspto-grants-2004_02
Patent number
US06689898B2

Reaction notes

Loading…