1,2-Dichlorobenzene → 2-Propenyl-4-cyclohexylphenol

HRID 843624Notes

Reaction equation

HRID 843624 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9](OCC=C)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:19]1[CH:24]=CC=C[C:20]=1Cl>>[CH:20]([C:9]1[CH:8]=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:12]=[CH:11][C:10]=1[OH:13])=[CH:19][CH3:24]

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 184146354-Cyclohexyl allyloxyphenol

Product 1

HCID 693539132-Propenyl-4-cyclohexylphenol

Procedure

A solution of 4-cyclohexyl allyloxyphenol (12.3 g) in ortho-dichlorobenzene (50 mL) was kept at reflux for 36 h. The mixture was cooled to room temperature and chromatographed over silica gel to afford 2-propenyl-4-cyclohexylphenol (11.0 g). This material was dissolved in methanol (150 mL) and hydrogenated over Pd/C (1.2 g) at 50 psi. The reaction was filtered through Celite and concentrated in vacuo to afford the title compound (11.0 g).

Workup

  1. temperatureat reflux for 36 h
  2. customchromatographed over silica gel

Sources & evidence

ORD record
ord-0cc6dd7519304df89750e2f7acf02c24
Source dataset
uspto-grants-2002_04
Patent number
US06380191B1

Reaction notes

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