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

HRID 2372668Notes

Reaction equation

HRID 2372668 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-toluene-sulfonic 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-2a793aa8881446e0b441cf024f6314d3
Source dataset
uspto-grants-1992_03
Patent number
US05100579

Reaction notes

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