Water → 6-Oxohexanoic acid

HRID 568865Notes

Reaction equation

HRID 568865 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8])=[O:2].O>S(=O)(=O)(O)O.CO>[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:2]

Participants

5

Reactant 2

HCID 962WaterHCID 81164Methyl 6-oxohexanoate

Product 1

HCID 4409186-Oxohexanoic acidYield 57%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

36 g of methyl 5-formylvalerate, 90 g of water and 0.5 g of sulfuric acid were refluxed for 3.5 hours, the methanol formed being distilled off constantly. Fractional distillation under reduced pressure gave 18.5 g (yield 57% of theory) of 5-formylvaleric acid of boiling point 106°-112° C./1 mbar. 13C NMR spectrum in D-chloroform: chemical shifts relative to tetramethyl silane as internal standard=21, 24, 34 and 44 ppm (4 methylene groups), 178 ppm (formyl group) and 203 ppm (carboxyl group).

Workup

  1. distillationbeing distilled off constantly
  2. distillationFractional distillation under reduced pressure

Sources & evidence

ORD record
ord-f5b7e8197c6a45ea831dc5394ba5ebaa
Source dataset
uspto-grants-1988_03
Patent number
US04730040

Reaction notes

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