Sodium Iodide → 1-[4-(4,4-Dimethylcyclohex-1-enyl)phenyl]ethanone

HRID 1018802Notes

Reaction equation

C[O:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2(O)[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(OC)[CH3:4].[I-].[Na+].C(#N)C.[Cl-].Cl[Si](C)(C)C>ClCCl.C(O)(=O)C>[CH3:19][C:16]1([CH3:20])[CH2:17][CH2:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:3](=[O:2])[CH3:4])=[CH:12][CH:11]=2)=[CH:14][CH2:15]1

Participants

Conditions

Temperature: 30 °C

Procedure

99.32 g of 1-[4-(1,1-dimethoxyethyl)phenyl]-4,4-dimethylcyclohexanol in 300 ml of dichloromethane, and 151 g of sodium iodide are added to 600 ml of acetonitrile, under an inert atmosphere, and the reaction mixture is heated to 30° C. 102 ml of chlorotrimethylsilane chloride are added, followed, at 65° C., by portionwise addition of a mixture of 300 ml of acetonitrile and 47 ml of acetic acid, and the reaction mixture is stirred for 12 hours at room temperature. The reaction mixture is filtered and extracted with dichloromethane. The residue obtained is purified by chromatography on a column of silica gel, eluting with a 99/1 (v/v) cyclohexane/ethyl acetate mixture.

Workup

filtrationThe reaction mixture is filtered
extractionextracted with dichloromethane
customThe residue obtained
customis purified by chromatography on a column of silica gel
washeluting with a 99/1 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record: ord-63feb7e9476b4b8f87daaaac5687fb61
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482986B1

Reaction notes

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