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

HRID 619994Notes

Reaction equation

HRID 619994 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-d9a8e1a1ff074b9eac699b46a051c338
Source dataset
uspto-grants-1989_04
Patent number
US04818525

Reaction notes

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