Water → 1-(4'-Acetylbiphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester

HRID 2391051Notes

Reaction equation

HRID 2391051 reaction equation
[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:26](Cl)(=[O:28])[CH3:27].O>C(Cl)Cl>[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:26](=[O:28])[CH3:27])=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 666602081-(Biphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester

Product 1

HCID 666602881-(4'-Acetylbiphenyl-4-yl)cyclopropanecarboxylic acid isopropyl esterYield 108.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(biphenyl-4-yl)cyclopropanecarboxylic acid isopropyl ester (10.2 g, 36 mmol) in CH2Cl2 (100 mL) was added aluminum chloride (10.2 g, 76.5 mmol) followed by acetyl chloride (5.97 g, 76.5 mmol). The solution was stirred at room temperature for 1.5 hours then slowly poured into water. The organic layer was separated and extracted 1 time with sodium potassium tartrate solution (20 g in 250 mL water). The organic layer was dried and evaporated to yield 12.6 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionextracted 1 time with sodium potassium tartrate solution (20 g in 250 mL water)
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-64a862f4c3a142938e97e3244ed2198c
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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