Ethyl Bromide → 4-Acetyl-4'-ethoxybiphenyl

HRID 1608748Notes

Reaction equation

HRID 1608748 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17](Br)[CH3:18].C(=O)([O-])[O-].[K+].[K+].C1(=O)CCCCC1>>[CH2:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH3:18]

Participants

5

Reactant 4

HCID 6332Ethyl BromideHCID 7967CyclohexanoneHCID 11430Potassium CarbonateHCID 103308064-(4-Acetylphenyl)phenol

Product 1

HCID 232504334-Acetyl-4'-ethoxybiphenyl

Procedure

A reaction vessel was charged with 230 g of 4-hydroxy-4'-acetylbiphenyl, 164 g of ethyl bromide, 276 g of potassium carbonate and 1.7 l of cyclohexanone. The mixture was reacted together under agitation for 3 hours at 65°-70° C. and then for 6 hours at 95°-100° C. The reaction liquid was filtered and the resultant solid matter was washed with benzene. The filtrate and the washing liquid were combined, washed with water and dried over Glauber's salt, The solvents were distilled off and the residue was recrystallized from a mixed solvent of acetone-methanol to obtain 4-ethoxy-4'-acetylbiphenyl.

Workup

  1. customThe mixture was reacted together under agitation for 3 hours at 65°-70° C.
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. washthe resultant solid matter was washed with benzene
  5. washwashed with water
  6. dry with materialdried over Glauber's salt
  7. distillationThe solvents were distilled off
  8. customthe residue was recrystallized from a mixed solvent of acetone-methanol

Sources & evidence

ORD record
ord-908052fa35794ecbae223747716a08f4
Source dataset
uspto-grants-1995_03
Patent number
US05397504

Reaction notes

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