Hydrochloric Acid → 4-Biphenylyl benzoate

HRID 2082109Notes

Reaction equation

HRID 2082109 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.Cl.O>N1C=CC=CC=1>[C:1]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 71034-HydroxybiphenylHCID 7412Benzoyl chloride

Product 1

HCID 2317434-Biphenylyl benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

128 ml benzoyl chloride is dripped into a solution of 170 g 4-hydroxybiphenyl in 500 ml pyridine, at 20° C.; subsequently, the reaction mixture is heated under reflux for 30 min. After cooling, the reaction mixture is mixed with a solution of 500 ml concentrated hydrochloric acid and 750 ml water. The remaining precipitate is filtered off, washed neutral with water, dried and recrystallized from n-butanol (melting point: 150° C.); yield: 94%.

Workup

  1. temperaturesubsequently, the reaction mixture is heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. filtrationThe remaining precipitate is filtered off
  5. washwashed neutral with water
  6. customdried
  7. customrecrystallized from n-butanol (melting point: 150° C.)

Sources & evidence

ORD record
ord-0c10c08e9eb6412ab234c4568d03deef
Source dataset
uspto-grants-1993_02
Patent number
US05187237

Reaction notes

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