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

HRID 2352585Notes

Reaction equation

HRID 2352585 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][C@@H:18]([CH2:21][CH3:22])[CH2:19]O.S(=O)(=O)(O)O>C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH:18]([CH3:19])[CH2:21][CH3:22])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 2723602(S)-2-methyl-1-butanol

Product 1

HCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

93 m mol (20 g) of 4'-hydroxybiphenyl-4-carboxylic acid and 467 m mol (41 g) of (S)-(-)-2-methylbutanol were refluxed for 25 hours in 150 ml of benzene in the presence of 2 ml of Conc. sulfuric acid while removing water. The resulting reaction solution was concentrated and was recrystallized from a toluene-hexane solvent mixture to obtain 26.0 g of the objective ester (m.p. 116-117.8° C., [α]D23 =+4.35° (CHCl3)). (Yield: 98 %).

Workup

  1. customwhile removing water
  2. customThe resulting reaction solution
  3. concentrationwas concentrated
  4. customwas recrystallized from a toluene-hexane solvent mixture

Sources & evidence

ORD record
ord-9e4a4c00644c40c789c5687a8ff48b2c
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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