4,4'-Dihydroxybiphenyl → HCID 23364889, compound

HRID 1080560Notes

Reaction equation

HRID 1080560 reaction equation
[CH:1]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)=[CH:5][CH:4]=[C:3]([OH:14])[CH:2]=1.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([O:14][C:3]2[CH:2]=[CH:1][C:6]([C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=3)=[CH:5][CH:4]=2)=[O:22])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 71124,4'-DihydroxybiphenylHCID 7477p-Anisoyl chloride

Product 1

HCID 23364889HCID 23364889, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-15 °C

Procedure

3.72 g of 4,4'-hydroxybiphenyl was put in an 100 ml two-necked. flask and dissolved by the addition of 60 ml of pyridine. The flask was set up in an ice bath. 3.41 g of 4-methoxybenzoyl chloride was added over 1.5 hours while maintaining the reaction mixture at -15° C. The mixture was reacted in the ice bath for 3 hours and then at an ambient temperature for 2 hours. The reaction mixture was poured into chipped ice to obtain a white precipitate. This precipitate was filtered, dried and re-crystallized with acetone. The yield was 63% and 1HNMR and IR spectra of the product were as follows.

Workup

  1. customThe flask was set up in an ice bath
  2. additionThe reaction mixture was poured into chipped ice
  3. customto obtain a white precipitate
  4. filtrationThis precipitate was filtered
  5. customdried
  6. customre-crystallized with acetone

Sources & evidence

ORD record
ord-79284e40ed9846d4b739fb9f86a33e58
Source dataset
uspto-grants-1996_12
Patent number
US05582766

Reaction notes

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