4-Hydroxybiphenyl → 4-Decyloxy-1,1'-biphenyl

HRID 1196441Notes

Reaction equation

HRID 1196441 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[K+]>C(OCC)(=O)C>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 81731-BromodecaneHCID 14797Potassium Hydroxide

Product 1

HCID 104956394-Decyloxy-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-1,1'-biphenyl (61.3 g, 0.36 mol) and decyl bromide (218 g, 0.72 mol) were heated at 80° C. To this solution, a 50% potassium hydroxide aqueous solution (57 g) was added dropwise at 80° C. and then stirring was continued for 6 h at the same temperature. After cooling, the mixture was diluted with ethyl acetate, the organic layer was separated, washed with H2O and dried over MgSO4. The solvent was removed under reduced pressure and the resultant residue was recrystallized from a mixed solvent of n-hexane and ethyl acetate to give the title compound as a white crystals; yield: 70 g (62.6%); mp 70.0°-73.0° C.

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. washwashed with H2O
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe resultant residue was recrystallized from a mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-8b8d3e61d17a4cca835e5d38c617c7ca
Source dataset
uspto-grants-1992_05
Patent number
US05114615

Reaction notes

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