4-Hydroxybiphenyl → 4-Acetoxybiphenyl

HRID 2410933Notes

Reaction equation

HRID 2410933 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[C:8]1([C:14]2[CH:19]=CC(O)=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)(=O)C>[C:5]([O:4][C:1]1[CH:16]=[CH:15][C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:2]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 71034-HydroxybiphenylHCID 7918Acetic Anhydride2×

Product 1

HCID 3460664-AcetoxybiphenylYield 95.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a 3-liter, 4-way flask equipped with a reflux cooling tube, 373.8 g of acetic anhydride and 248.0 g (1.46 mol) of 4-phenylphenol were introduced and the mixture was heated to cause reaction for 3 hours under agitation while keeping the temperature in the flask at 130° C. After the reaction, the reflux pipe was replaced with a distillation pipe and acetic anhydride and acetic acid were removed by distillation under decompression, after which n-heptane was added and the mixture was cooled. The precipitated crystal was filtered out and dried to obtain 296.8 g of 4-acetoxybiphenyl in a white crystal form. The yield relative to the material 4-phenylphenol was 96% (mol).

Workup

  1. customInto a 3-liter, 4-way flask equipped with a reflux
  2. temperaturecooling tube
  3. temperaturethe mixture was heated
  4. customreaction for 3 hours under agitation
  5. customat 130° C
  6. customAfter the reaction
  7. customwere removed by distillation under decompression
  8. additionafter which n-heptane was added
  9. temperaturethe mixture was cooled
  10. filtrationThe precipitated crystal was filtered out
  11. customdried

Sources & evidence

ORD record
ord-b137eaf787404a10819219a758135071
Source dataset
uspto-grants-2014_08
Patent number
US08816135B2

Reaction notes

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