Anisole, p-1-cyclohexen-1-yl- → Phenol, p-(1-cyclohexen-1-yl)-

HRID 1764125Notes

Reaction equation

HRID 1764125 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.N1C=CC=CC=1>O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 253825Anisole, p-1-cyclohexen-1-yl-HCID 10176127Pyridinium chloride

Product 1

HCID 69727Phenol, p-(1-cyclohexen-1-yl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

56.5 Grams of p-(1-cyclohexenyl)-anisol and 125 g of pyridine-hydrochloride are thoroughly mixed and heated for 3 hours in an atmosphere of nitrogen to 180° C. The reaction mixture is cooled to room temperature, treated with water and extracted with 3 × 400 ml of benzene. The benzene extracts are washes with 3 × 300 ml of water, dried over sodium sulphate and evaporated in vacuo. The solid residue yields the crude p-(1-cyclohexenyl)-phenol (m.p. 115-119° C), which can be purified by recrystallisation from benzene and then melts at 120°-122° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionextracted with 3 × 400 ml of benzene
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7a63c0b80e93477dbaade6ac592abf63
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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