p-Toluenesulfonic acid → HCID 20206193, compound

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])CO)[CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:21]([CH2:19][CH3:20])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:14]

Participants

Procedure

5.0 parts of methyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate, 50 parts of 2-ethyl-hexanol and 0.5 parts of p-toluene sulphonic acid are heated on a steam-bath for 18 hours. The reaction mixture is then diluted with ether, washed with sodium bicarbonate solution, water, and evaporated. The residue, after stripping off excess 2-ethylhexanol on a rotary evaporator at 100° C. and 0.13 mb pressure gives 2-ethylhexyl 5-(2,4-dihydroxyphenyl)-5-methylhexanoate as a viscous amber liquid with the following percentage composition by weight.