Water → Ethyl 1-(4'-acetyl-[1,1'-biphenyl]-4-yl)cyclopropanecarboxylate

HRID 2391046Notes

Reaction equation

HRID 2391046 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:25](Cl)(=[O:27])[CH3:26].O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:25](=[O:27])[CH3:26])=[CH:19][CH:20]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 66660499Ethyl 1-([1,1'-biphenyl]-4-yl)cyclopropanecarboxylate

Product 1

HCID 66660270Ethyl 1-(4'-acetyl-[1,1'-biphenyl]-4-yl)cyclopropanecarboxylateYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(biphenyl-4-yl)cyclopropanecarboxylic acid ethyl ester (9 g, 33.8 mmol) in CH2Cl2 (100 mL) was added aluminum chloride (9.4 g, 71 mmol) followed by acetyl chloride (5.5 g, 71 mmol). The solution was stirred at room temperature for 1.5 hours then slowly poured into water. The organic layer was separated and extracted 2 times with water. The organic layer was dried and evaporated to yield 11.3 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionextracted 2 times with water
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-1a70aa9ec3324c328adaeb9c26071ae6
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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