Diethyl Ether → Diisopropyl ether pentane

HRID 430719Notes

Reaction equation

HRID 430719 reaction equation
[CH3:1][C:2]([C:4]1C=CC=[C:6](Cl)[CH:5]=1)=[O:3].O.[C:12](O)(=O)[CH:13]=O.[CH2:17](OCC)C>C(Cl)Cl.CO>[CH:13]([O:3][CH:2]([CH3:1])[CH3:4])([CH3:12])[CH3:17].[CH3:1][CH2:2][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 149331-(3-Chlorophenyl)ethanoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 86614970Diisopropyl ether pentane

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

A well stirred mixture of 3-chloroacetophenone (18.9 g, 0.1 mol) and glyoxylic acid monohydrate (9.2 g, 0.1 mol) was heated at 60° C. under vacuum (25 mmHg), over 16 hours. The residue was taken up with diethyl ether and the organic phase was extracted with saturated NaHCO3 solution, the combined aqueous layers were whased with ether, cooled at 0° C. and the pH of the solution was adjusted to 2 by addition of 37% HCl. The resulting suspension was extracted with ethyl acetate, and the combined organic extracts washed with water, drided (Na2SO4) and concentrated in vacuo to provide the crude product. Column chromatography (SiO2; CH2Cl2/MeOH 95:5) afforded the pure titled compound as colorless needles, mp.98-100° C. (Diisopropyl ether/pentane).

Workup

  1. extractionthe organic phase was extracted with saturated NaHCO3 solution
  2. temperaturecooled at 0° C.
  3. additionthe pH of the solution was adjusted to 2 by addition of 37% HCl
  4. extractionThe resulting suspension was extracted with ethyl acetate
  5. washthe combined organic extracts washed with water
  6. concentrationconcentrated in vacuo
  7. customto provide the crude product

Sources & evidence

ORD record
ord-6375eeb5496b4a3cac8ce7b187cf17cc
Source dataset
uspto-grants-2001_11
Patent number
US06323240B1

Reaction notes

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