Sulfuric Acid → 2-Ethylhexyl 6-methylheptanoate

HRID 726933Notes

Reaction equation

HRID 726933 reaction equation
S(=O)(=O)(O)O.[CH2:6]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][OH:10])[CH3:7].[C:15](O)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[CH2:6]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][O:10][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 77202-EthylhexanolHCID 907166-Methylheptanoic acid

Product 1

HCID 197046032-Ethylhexyl 6-methylheptanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 g concentrated sulfuric acid were added to a solution of 130 g (1 mol) 2-ethylhexanol and 144 g (1 mol) "isooctanoic acid" (isomeric mixture from Ruhrchemie A. G., Oberhausen) in 300 ml toluene and heated to boiling with water 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 remaining end-product gave after distillation over a 15 cm Vigreux column 230 g (90%) isooctanoic acid-2-ethyl-hexylester as a colorless oil of medium viscosity.

Workup

  1. temperatureheated
  2. customto boiling with water separation until the equimolar amount of water
  3. custom(about 2 hours)
  4. temperatureAfter cooling it
  5. washwas washed with water
  6. customThe remaining end-product gave
  7. distillationafter distillation over a 15 cm Vigreux column 230 g (90%) isooctanoic acid-2-ethyl-hexylester as a colorless oil of medium viscosity

Sources & evidence

ORD record
ord-240ae9a62b0e46d4906595b02a86672f
Source dataset
uspto-grants-1998_01
Patent number
US05711939

Reaction notes

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