Acetic Acid → 2-Tert-butyl-6-cyclohexen-1-yl-4-methoxyphenol

HRID 1584529Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.Cl>CCCCCC>[C:1]([C:5]1[CH:6]=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([C:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=2)[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture consisting of 36.1 g (0.20 mol) of 3-tert-butyl-4-hydroxyanisol, 19.6 g (0.20 mol) of cyclohexanone and 10 ml of acetic acid is placed in a reactor and saturated, with stirring, with hydrochloric acid gas at room temperature. After standing for 64 hours at room temperature, the mixture is again saturated with hydrochloric acid gas and stirred for another 5 hours at 40° C. The reaction mixture is diluted with hexane and washed with water, sodium chloride solution and sodium hydrogencarbonate solution. 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 ethyl acetate/hexane=1:49, giving 15.1 g (29%) of 2-tert-butyl-6-cyclohexen-1-yl-4-methoxyphenol as a yellowish thick oil, 1H--NMR (CDCl3), δ(ppm): 3.75 (s, 3H, OCH3), 5.87 (m, 1H, cyclohexenyl--H), (compound (111), Table 1).

Workup

customis placed in a reactor
washwashed with water, sodium chloride solution and sodium hydrogencarbonate solution
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 ethyl acetate/hexane=1:49

Sources & evidence

ORD record: ord-8d80bfad7bd14b8881581d9877a7ee69
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932642

Reaction notes

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