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

HRID 2072652Notes

Reaction equation

HRID 2072652 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-4cc25d9bf69542d2b416005f581191de
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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