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

HRID 2231340Notes

Reaction equation

HRID 2231340 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 refluxed for 8 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with benzene. The benzene solution was washed with water and dried, and benzene was evaporated under reduced pressure. The resulting oily product was purified by column chromatography (silica gel; eluent: benzene) to give 4.2 g of 1-(3-phenoxyphenyl)-4-(4-hydroxyphenyl)-4-methylpentane.

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionextracted with benzene
  3. washThe benzene solution was washed with water
  4. customdried
  5. custombenzene was evaporated under reduced pressure
  6. customThe resulting oily product was purified by column chromatography (silica gel; eluent: benzene)

Sources & evidence

ORD record
ord-0f366e65ecc84e368e2b98b6c2d028bb
Source dataset
uspto-grants-1988_11
Patent number
US04782094

Reaction notes

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