Phosphoric Acid → 4-Ketotridec-2-enoic acid

HRID 326353

Reaction equation

HRID 326353 reaction equation
[CH3:1][C:2](=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].O.[C:14]([OH:18])(=[O:17])[CH:15]=O.P(=O)(O)(O)O>C(OCC)C.ClCCl>[O:12]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:1]=[CH:15][C:14]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 81632-UndecanoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 540772154-Ketotridec-2-enoic acid

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A mixture of 2-undecanone (10 g, 58.7 mmol), glyoxylic acid monohydrate (5.15 g, 56 mmol) and 85% phosphoric acid (10 ml) was warmed at 80° for 18 hours. On cooling to room temperature, the mixture was diluted with ethyl ether/dichloromethane (50 ml each) and washed thoroughly with brine. Evaporation of the dried (magnesium sulphate) organic phase gave a yellow oil which on crystallization from ethyl ether/petroleum ether gave 4-ketotridec-2-enoic acid as colorless prisms.

Workup

  1. temperaturewas warmed at 80° for 18 hours
  2. washwashed thoroughly with brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate) organic phase
  5. customgave a yellow oil which
  6. customon crystallization from ethyl ether/petroleum ether

Sources & evidence

ORD record
ord-19d75f4641b8449e884f3b2e060b0af9
Source dataset
uspto-grants-1993_12
Patent number
US05268387

Linked notes

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