Sulfuric Acid → 2-Methylbutyl 4'-hydroxybiphenyl-4-carboxylate

HRID 482814Notes

Reaction equation

HRID 482814 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:17][CH:18]([CH2:21][CH3:22])[CH2:19]O.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:17][CH:18]([CH2:21][CH3:22])[CH2:19][O:15][C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 87232-Methyl-1-butanolHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20 g of 4-hydroxy-4'-biphenylcarboxylic acid, 53 g of (-)2-methylbutanol, and 4 g of conc. sulfuric acid were refluxed for 20 minutes, admixed with 500 ml of benzene, and heated in a container provided with a Dean-Stark reflux condenser. Generated water was removed. After the reaction mother liquor was cooled and washed with water, the solvent was distilled off to obtain crude 4-hydroxy-4'-biphenylcarboxylic acid 2-methylbutyl ester. The product was recrystallized from benzene-heptane mixed solvent to obtain a purified product having a melting point of 115° to 116° C.

Workup

  1. temperatureheated in a container
  2. customprovided with a Dean-Stark
  3. temperaturereflux condenser
  4. customGenerated water was removed
  5. temperatureAfter the reaction mother liquor was cooled
  6. washwashed with water
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0b1945abc18a43dd8acfc2dcf7fb74a6
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

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