p-Toluenesulfonic acid → (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid

HRID 849613Notes

Reaction equation

O[C:2]1([C:16]([OH:18])=[O:17])[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][C:3]1([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:5][C:6](=[O:8])[CH:7]=[C:2]1[C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

4.4 g (17.6 mmol) of (1RS,2RS)-1-hydroxy-2-methyl-5-oxo-2-phenylcyclohexane-1-carboxylic acid were heated at reflux for one hour in 100 cm3 of toluene in the presence of 0.34 g of para-toluenesulphonic acid. The reaction mixture was cooled to 0° C. and the precipitate formed was filtered off, washed with ethyl ether and then dried at 50° C. 2.8 g (69%) of (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid were thus obtained in the form of a pink solid, the characteristics of which were as follows:

Workup

customthe precipitate formed
filtrationwas filtered off
washwashed with ethyl ether
customdried at 50° C

Sources & evidence

ORD record: ord-eb8e01f511f04a33a5da969205bb9657
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013662

Reaction notes

Loading…