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

HRID 543272Notes

Reaction equation

HRID 543272 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% aq HBr and 30 ml of acetic acid was refluxed with heating for eight hours. The reaction mixture was poured into water and extracted with benzene. The benzene extract was washed with water and dried, and the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: benzene) to give 4.2 g of 1-(3-phenoxyphenyl)-4-(4-hydroxyphenyl)-4-methylpentane.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for eight hours
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. washwas washed with water
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: benzene)

Sources & evidence

ORD record
ord-d001468ee973417b83b7c04843ecccf2
Source dataset
uspto-grants-1987_04
Patent number
US04661501

Reaction notes

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