Ethanol → 2-Methylhexanoic Acid

HRID 2225958Notes

Reaction equation

HRID 2225958 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([C:17](C)([C:23](OCC)=O)[C:18]([O:20]CC)=[O:19])[CH2:14][CH2:15][CH3:16].C(O)C>O>[CH3:23][CH:17]([CH2:13][CH2:14][CH2:15][CH3:16])[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 41326Diethyl butylmethylmalonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 206532-Methylhexanoic AcidYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 40 g of p-toluenesulfonic acid monohydrate and 313 g of diethyl butylmethylmalonate was heated to 125°-135° C. in a flask equipped with a distillation column packed with Raschig rings. After 15 minutes, ethanol began to reflux in the distillation head. Ethanol was distilled as it formed and the pot temperature was maintained at 120°-126° C. by periodic addition of water to the pot. After 22 hours, the distillation of ethanol had ceased. The mixture then was cooled and treated with 70 ml of water. The layers were separated to afford 159.2 g (90.6% yield) of 2-methylhexanoic acid (99.8% pure by VPC).

Workup

  1. temperaturewas heated to 125°-135° C. in a flask
  2. customequipped with a distillation column
  3. temperatureto reflux in the distillation head
  4. distillationEthanol was distilled as it
  5. customformed
  6. waitAfter 22 hours
  7. distillationthe distillation of ethanol
  8. temperatureThe mixture then was cooled
  9. additiontreated with 70 ml of water
  10. customThe layers were separated

Sources & evidence

ORD record
ord-2d9f9e0b189e4647afd9fe72eeff78d2
Source dataset
uspto-grants-1994_09
Patent number
US05344975

Reaction notes

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