(4S)-4-[(Hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane → (2R)-3-(Hexadecyloxy)-1,2-propanediol

HRID 1885485Notes

Reaction equation

HRID 1885485 reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]1[CH2:23][O:22]C(C)(C)[O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CO.Cl>[CH2:1]([O:17][CH2:18][C@H:19]([OH:20])[CH2:23][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 13916252(4S)-4-[(Hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 11758911(2R)-3-(Hexadecyloxy)-1,2-propanediolYield 73.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A stirred mixture of 28 g of (S)-4-[(hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane in 190 ml of methyl alcohol and 21 ml of 1N hydrochloric acid is refluxed for 2 hours followed by cooling in an ice bath. The resulting solid is filtered and washed with cold acetone. The solid is crystallized from acetone to give 18.2 g of crystals which liquified at ambient temperature. The resulting oil is purified by chromatography on silica gel using 1:1 ethyl acetate:hexanes. Fractions containing product are combined and evaporated to a material which is stirred with acetone at -20° C. to give 4.1 g of crystalline solid, m.p. 65°-66° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureby cooling in an ice bath
  3. filtrationThe resulting solid is filtered
  4. washwashed with cold acetone
  5. customThe solid is crystallized from acetone

Sources & evidence

ORD record
ord-d37ea3f476154b719562c5aef3672d56
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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