Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-2-cyclopropylethan-1-one

HRID 964738Notes

Reaction equation

HRID 964738 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:23])[CH2:19][CH:20]2[CH2:22][CH2:21]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C.ClCCl.ClCCl.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:23])[CH2:19][CH:20]2[CH2:21][CH2:22]2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanol

Product 1

HCID 134886181-(4-Chlorophenyl)-2-cyclopropylethan-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21699599Dichloromethane methaneSolvent

Procedure

Oxalyl chloride (14.3 ml, 160 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (14.3 ml, 200 mmol) in dry dichloro-methane methane (350 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (12.98 g, 66 mmol) in dry dichloromethane (120 ml) was added to the mixture. After an hour triethylamine (71.4 ml), 510 mmol) was added and the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the combined extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe combined extracts washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-31d57bbd0ab44162ab80fa5051c75a86
Source dataset
uspto-grants-1998_06
Patent number
US05770741

Reaction notes

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