Isopropanol → HCID 13982253, compound

HRID 414772Notes

Reaction equation

HRID 414772 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:30][CH2:31][C@H:32]1[C@H:37]([OH:38])[CH2:36][CH2:35][CH2:34][O:33]1)[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][CH2:28][CH3:29].C(O)(C)C>CC(C)=O.C(OCC)(=O)C>[CH2:14]([O:30][CH2:31][CH:32]1[C:37](=[O:38])[CH2:36][CH2:35][CH2:34][O:33]1)[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][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 22841027HCID 22841027, compoundHCID 131709961Jones' reagent

Product 1

HCID 13982253HCID 13982253, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 ml of Jones reagent (1.34 g as chromic anhydride) were added, whilst ice-cooling, to a solution of 4.30 g of dl-trans-2-hexadecyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 2) in 20 ml of acetone. The mixture was then stirred at room temperature for 2 hours, after which 2 ml of isopropanol were added. The reaction mixture was then stirred for a further 10 minutes, after which it was diluted with 50 ml of ethyl acetate and then washed, in turn, with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. It was then dried, and the solvent was removed by distillation. The resulting oily residue, 4.5 g, was subjected to column chromatography through 100 g of silica gel. The fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:10 to 3:20 by volume gave 3.73 g of the title compound, melting at 42°-43.5° C. (hexane).

Workup

  1. stirringThe reaction mixture was then stirred for a further 10 minutes
  2. washwashed, in turn, with water
  3. customIt was then dried
  4. customthe solvent was removed by distillation
  5. washThe fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:10 to 3:20 by volume

Sources & evidence

ORD record
ord-58bbd87af8404d008939b9e47e3818b8
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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