Methanol → Isooctanoic acid, methyl ester

HRID 726932Notes

Reaction equation

HRID 726932 reaction equation
S(=O)(=O)(O)O.[CH3:6]O.[C:8]([OH:17])(=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH3:6][O:16][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 907166-Methylheptanoic acid

Product 1

HCID 520188Isooctanoic acid, methyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 g concentrated sulfuric acid were added to a solution of 32 g (1 mol) methanol and 144 g (1 mol) "isooctanoic acid" (isomeric mixture from Ruhrchemie A. G. Oberhausen) in 200 ml toluene and heated to boiling with hater separation until the equimolar amount of water separates (about 2 hours). After cooling it was washed with water and then with 10% sodium bicarbonate solution. The solvent was distilled off under reduced pressure. The remaining end-product after distillation over a 15 cm Vigreux column gave 150 g (95%) isooctanoic acid methylester as an easily mobile liquid with a fruity smell.

Workup

  1. temperatureheated
  2. customto boiling with hater separation until the equimolar amount of water
  3. custom(about 2 hours)
  4. temperatureAfter cooling it
  5. washwas washed with water
  6. distillationThe solvent was distilled off under reduced pressure
  7. distillationThe remaining end-product after distillation over a 15 cm Vigreux column

Sources & evidence

ORD record
ord-0c6dfbe37cd349e9a97680f755d18529
Source dataset
uspto-grants-1998_01
Patent number
US05711939

Reaction notes

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