Thionyl Chloride → 1-Hydroxycyclohexyl 4-(2-chloroformylethyl)carbonylphenyl ketone

HRID 1977540Notes

Reaction equation

[C:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1)=[O:7])(O)=[O:2].S(Cl)([Cl:25])=O>C(OCC)C>[Cl:25][C:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1)=[O:7])=[O:2]

Participants

Conditions

Temperature: 30 °C

Procedure

A 250-ml round-bottomed flask fitted with a condenser was charged with 12.0 g of 1-hydroxycyclohexyl 4-(2-carboxyethyl)carbonylphenyl ketone (0.04 mole), 5.95 g (0.05 mole) of thionyl chloride (Aldrich Chemical Co., Milwaukee, Wis.), and 50 ml of diethyl ether. The resulting reaction mixture was stirred at 30° C. for 30 minutes, after which time the solvent was removed under reduced pressure. The residue, a lwhite solid, was maintained at 0.01 Torr for 30 minutes to remove residual solvent and excess thionyl chloride, leaving 12.1 g (94 percent) of 1-hydroxycyclohexyl 4-(2-chloroformylethyl)carbonylphenyl ketone.

Workup

customA 250-ml round-bottomed flask fitted with a condenser
customThe resulting reaction mixture
customafter which time the solvent was removed under reduced pressure
temperatureThe residue, a lwhite solid, was maintained at 0.01 Torr for 30 minutes
customto remove residual solvent and excess thionyl chloride

Sources & evidence

ORD record: ord-e733c434d6e649b2a6cafc39e15f932c
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235095B1

Reaction notes

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