Methyl Ethyl Ketone → HCID 21474593, compound

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7](=O)[CH2:6][CH:5]=[CH:4][C:3]1=2.[OH:16][C:17]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([OH:28])[C:18]=1[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].[CH2:35]([C:37](C)=[O:38])C>>[OH:16][C:17]1[CH:26]=[C:25]([O:27][CH2:35][C:37]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:38])[CH:24]=[C:23]([OH:28])[C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

Reactant 4

HCID 6569Methyl Ethyl Ketone

HCID 11430Potassium Carbonate

HCID 76600Methyl 2,4,6-trihydroxybenzoate

HCID 86751137HCID 86751137, compound

Product 1

HCID 21474593HCID 21474593, compound

Procedure

3.1 g (10 mmol) of 2-(2'-bromoaceto)-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthone, 1.8 g (10 mmol) of methyl 2,4,6-trihydroxybenzoate, 1.4 g (10 mmol) of potassium carbonate and 100 ml of methyl ethyl ketone are introduced into a flask. The mixture is heated under reflux for 1 hour and evaporated to dryness. The residue is taken up with water and dichloromethane, and the organic phase is separated, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column, eluted with a mixture of dichloromethane and hexane (50:50). After evaporation of the solvents, 2.2 g (53%) of the expected product of melting point 169°-170° C. are collected.