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

HRID 557621Notes

Reaction equation

HRID 557621 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-db860ed1db4c47fc8f8042d9bff2b5c7
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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