Hexane → 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one

HRID 1074318Notes

Reaction equation

HRID 1074318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:14])[CH:9]([CH:11]2[CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.CCCCCC>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:14])[CH:9]([CH:11]2[CH2:13][CH2:12]2)[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 8471TriethylamineHCID 190783851-(4-Chlorophenyl)-2-cyclopropylpropan-1-ol

Product 1

HCID 134886191-(4-Chlorophenyl)-2-cyclopropylpropan-1-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylpropan-1-ol (44.72 g, 212 mmol) in dry dichloromethane (330 ml) was added over approximately 35 minutes. After 75 minutes triethylamine (154 ml), 1105 mmol) was added and the mixture allowed to warm to room temperature. Hexane was added and the mixture washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate solution and water, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (100:0) to (90:10)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one (38.0 g, 86%).

Workup

  1. washthe mixture washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate solution and water
  2. customdried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c83872dbc42b4e8ab42ab55217af0e02
Source dataset
uspto-grants-1990_11
Patent number
US04973767

Reaction notes

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