Hydrochloric Acid → 2-Cyclohexen-1-yl-4,6-bis(1-methyl-1-phenylethyl)phenol

HRID 1584528Notes

Reaction equation

[CH3:1][C:2]([C:10]1[CH:15]=[C:14]([C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[OH:25])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[C:26]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.Cl>>[C:26]1([C:12]2[CH:13]=[C:14]([C:16]([CH3:17])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[CH:15]=[C:10]([C:2]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)([CH3:1])[CH3:3])[C:11]=2[OH:25])[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid2×

HCID 7967Cyclohexanone2×

HCID 760132,4-Dicumylphenol

Product 1

HCID 570012212-Cyclohexen-1-yl-4,6-bis(1-methyl-1-phenylethyl)phenolYield 3.2%

Procedure

A mixture consisting of 66.1 g (0.20 mol) of 2,4-bis(1-methyl-1-phenylethyl)phenol and 9.8 g (0.10 mol) of cyclohexanone is melted together and is then saturated, with stirring, with hydrochloric acid gas at 40-45° C. After 19 hours, another 9.8 g (0.10 mol) of cyclohexanone are added. The reaction mixture is saturated again with hydrochloric acid gas and is then stirred for 21 hours. The reaction mixture is diluted with petroleum ether and washed with water. The organic phase is dried over magnesium sulfate and concentrated on a rotary evaporator. The residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=39:1, giving 1.3 g (2%) of 2-cyclohexen-1-yl-4,6-bis(1-methyl-1-phenylethyl)phenol as a thick yellowish oil (compound (110), Table 1).

Workup

washwashed with water
dry with materialThe organic phase is dried over magnesium sulfate
concentrationconcentrated on a rotary evaporator
customThe residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=39:1

Sources & evidence

ORD record: ord-7b03cc7739ec46f4b9a14ca356c224b7
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932642

Reaction notes

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