Hydrochloric Acid → 4-(Cyclopropylcarbonyl)benzeneacetic acid

HRID 48016

Reaction equation

HRID 48016 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-f53ba3c5e8524a56b25ef814a2ac2587
Source dataset
uspto-grants-2004_03
Patent number
US06700012B2

Linked notes

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