Phosphoric Acid → HCID 57294103, compound

HRID 273946Notes

Reaction equation

HRID 273946 reaction equation
[CH3:1][C:2](=[O:6])[CH2:3][CH2:4][CH3:5].O.[C:8]([OH:12])(=[O:11])[CH:9]=O.P(=O)(O)(O)O>C(OCC)C.ClCCl>[O:6]=[C:2]([CH2:3][CH2:4][CH3:5])[CH:1]=[CH:9][C:8]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 78952-PentanoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 57294103HCID 57294103, compound

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A mixture of 2-pentanone (17.1 g, 198 mmol), glyoxylic acid monohydrate (8.05 g, 88 mmol) and about 85% phosphoric acid (12 ml) was warmed at ca. 80° for 19 hours. On cooling to room temperature the mixture was diluted with ethyl ether/dichloromethane (100 ml, 1:1) and washed thoroughly with brine. Evaporation of the dried (magnesium sulphate) organic phase gave a yellow viscous oil, which on crystallization from ethyl ether/petroleum ether gave 4-keto-hept-2-enoic acid as colorless prisms: mp 100°-2°.

Workup

  1. temperaturewas warmed at ca. 80° for 19 hours
  2. washwashed thoroughly with brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate) organic phase
  5. customgave a yellow viscous oil, which
  6. customon crystallization from ethyl ether/petroleum ether

Sources & evidence

ORD record
ord-ef6ed92d25804f4da17f566311f97b11
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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