Benzene → 2-Methylbutyl 4'-hydroxybiphenyl-4-carboxylate

HRID 568318Notes

Reaction equation

HRID 568318 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:17][C@@H:18]([CH2:21][CH3:22])[CH2:19]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[CH3:17][CH:18]([CH2:21][CH3:22])[CH2:19][O:13][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 2723602(S)-2-methyl-1-butanol

Product 1

HCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Five grams of 4-(4'-hydroxyphenyl)benzoic acid, 5 g of (s)-2-methylbutylalcohol and 11 g of p-toluenesulfonic acid were dissolved with 50 ml of benzene. Occurred water in the mixture was removed by azotropic dehydration with refluxing for eight hours. After adding 50 ml of water to the residue, the organic phase was concentrated to obtain 4-(4'-hydroxyphenyl)benzoic acid-2-methylbutyl ester (BJ).

Workup

  1. customwas removed by azotropic dehydration
  2. temperaturewith refluxing for eight hours
  3. additionAfter adding 50 ml of water to the residue
  4. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-a563e3a17d40442f91cb55e963810c95
Source dataset
uspto-grants-1988_03
Patent number
US04728458

Reaction notes

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