Hydrochloric Acid → HCID 22390439, compound

HRID 1071928Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([Cl:14])[CH:8]=1.[CH3:15][C:16]1([CH3:23])[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1.Cl>CCCCCC.O1CCCC1>[Cl:14][C:9]1[CH:8]=[C:7]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]([CH3:23])([CH3:15])[CH2:17][CH2:18]2)[CH:12]=[CH:11][C:10]=1[OH:13]

Participants

Conditions

Temperature: -78 °C

Procedure

100 ml of a 1.6 M solution of butyllithium in hexane are added at −78° C. to 15.1 g of 4-bromo-2-chlorophenol in 150 ml of tetrahydrofuran, and the reaction mixture is stirred for 1 hour at −78° C. 10.1 g of 4,4-dimethylcyclohexanone (compound 3.1) are added and the reaction mixture is stirred at −78° C. for a further 30 minutes and then at room temperature for 12 hours. The reaction mixture is hydrolysed with 1N hydrochloric acid solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The solid obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/ethyl acetate mixture which varies from 98/2 to 90/10 (v/v). 11.8 g of solid are obtained.

Workup

stirringthe reaction mixture is stirred at −78° C. for a further 30 minutes
waitat room temperature for 12 hours
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulphate
customthe solvents are evaporated off under reduced pressure
customThe solid obtained
customis purified by chromatography on a column of silica gel
washeluting with a cyclohexane/ethyl acetate mixture which

Sources & evidence

ORD record: ord-669149fcb03c4947a995a444cf420c1f
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908914B1

Reaction notes

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