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

HRID 964734Notes

Reaction equation

HRID 964734 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-f7e7b9d6cb45407a8d9c07924a7f30e0
Source dataset
uspto-grants-1998_06
Patent number
US05770741

Reaction notes

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