4-Hydroxybenzoic Acid → 4-(1-Methylheptyloxycarbonyl)phenol

HRID 231025

Reaction equation

HRID 231025 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C@@H:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:11][CH:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 80080(R)-2-Octanol

Product 1

HCID 110103794-(1-Methylheptyloxycarbonyl)phenolYield 43%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

27.6 g of p-hydroxybenzoic acid and 39.0 g of (R)-2-octanol were refluxed for 10 hours in 300 ml of benzene in the presence of 0.5 ml of conc. sulfuric acid. Then, the reaction solution was cooled to the room temperature, and then concentrated and purified by column chromatography, to obtain 21.5 g of p-hydroxybenzoic acid 1-methylheptyl ester. (yield: 43%)

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-9a63337d10b54f90af339903302db2f4
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Linked notes

Loading…