Acetic Acid → Phenol, 4-[1,1-dimethyl-4-(3-phenoxyphenyl)butyl]-

HRID 358553Notes

Reaction equation

HRID 358553 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(O)(=O)C>O>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 135322971-[4-(4-Methoxyphenyl)-4-methylpentyl]-3-phenoxybenzene

Product 1

HCID 10980903Phenol, 4-[1,1-dimethyl-4-(3-phenoxyphenyl)butyl]-Yield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methylpentane, 30 ml of 47% hydrobromic acid and 30 ml of acetic acid was heated under reflux for 8 h. After cooling to room temperature, the reaction mixture was poured into water. After extraction with benzene, the benzene solution was washed with water and dried. Benzene was distilled off under reduced pressure and the obtained oily product was purified according to column chromatography (silica gel, developer: benzene) to obtain 4.2 g of 1-(3-phenoxyphenyl)-4-(4-hydroxyphenyl)-4-methylpentane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. extractionAfter extraction with benzene
  4. washthe benzene solution was washed with water
  5. customdried
  6. distillationBenzene was distilled off under reduced pressure
  7. customthe obtained oily product was purified

Sources & evidence

ORD record
ord-3ac93eef14744a38b9694c3a24f98de4
Source dataset
uspto-grants-1991_03
Patent number
US04997650

Reaction notes

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