2-Methyl-beta-octadecyl-1,3-dioxolan-2-propanol → 4-(Hydroxymethyl)-2-docosanone

HRID 235708Notes

Reaction equation

HRID 235708 reaction equation
[CH3:1][C:2]1([CH2:7][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][OH:10])OCC[O:3]1>CC(C)=O>[OH:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][C:2](=[O:3])[CH3:1]

Participants

3

Reactant 1

HCID 202189492-Methyl-beta-octadecyl-1,3-dioxolan-2-propanol

Product 1

HCID 202184114-(Hydroxymethyl)-2-docosanoneYield 65.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of about 21 g of 2-methyl-β-octadecyl-1,3-dioxolan-2-propanol in about 220 ml of acetone, about one ml of concentrated (about 12N) hydrochloric acid and about 15 ml of water was refluxed for about 20 minutes, poured into a solution of saturated sodium chloride and extracted with ether. The ether extract was washed with aqueous sodium bicarbonate, dried and the solvent removed. The residue was chromatographed via HPLC, eluting with hexane:ethyl acetate (about 9:1). The solvent was removed from the product fraction, giving about 12.3 g of the desired title compound as a white solid.

Workup

  1. concentrationof concentrated (about 12N) hydrochloric acid and about 15 ml of water
  2. temperaturewas refluxed for about 20 minutes
  3. additionpoured into a solution of saturated sodium chloride
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with aqueous sodium bicarbonate
  7. customdried
  8. customthe solvent removed
  9. customThe residue was chromatographed via HPLC
  10. washeluting with hexane
  11. customThe solvent was removed from the product fraction

Sources & evidence

ORD record
ord-606260c6c8ca4cd9ba0322971ea5c899
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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