Ethanol → Ethyl 3-oxohexanoate

Reaction equation

[CH2:1]([CH:5]1C(=O)O[C:8](C)([CH3:12])[O:7][C:6]1=[O:14])[CH2:2][CH2:3][CH3:4].C([OH:17])C>>[O:17]=[C:1]([CH2:2][CH2:3][CH3:4])[CH2:5][C:6]([O:7][CH2:8][CH3:12])=[O:14]

Participants

Reactant 2

HCID 702Ethanol

HCID 110634455-butyl-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 238498Ethyl 3-oxohexanoateYield 72%

Procedure

The 5-butyl-2,2-dimethyl-1,3-dioxane-4,6-dione thus obtained was allowed to reflux in ethanol for 2 hours, and then concentrated under reduced pressure. The resulting residue was purified using silica gel chromatography (developing solvent: n-hexane/ethyl acetate=8/2) to obtain the ethyl 3-oxohexanoate shown by the formula below.

Workup

concentrationconcentrated under reduced pressure
customThe resulting residue was purified

Sources & evidence

ORD record: ord-126cd627a5554cf8ad46da2674d9cdd7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436210B2

Reaction notes

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