HCID 10991921, compound → (S)-3-(Hexadecyloxy)propane-1,2-diol

HRID 248164Notes

Reaction equation

HRID 248164 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 10991921HCID 10991921, compound

Product 1

HCID 10448487(S)-3-(Hexadecyloxy)propane-1,2-diolYield 81.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 28.2 g of (R)-4-[(hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane in 189 ml of methyl alcohol and 21 ml of 1N hydrochloric acid is stirred at reflux for 2.5 hours followed by 12 hours at ambient temperature. The reaction is cooled, filtered and the cake washed with cold methyl alcohol then dried to give 20.3 g of the desired product as white plates, m.p. 63°-64° C.

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction is cooled
  3. filtrationfiltered
  4. washthe cake washed with cold methyl alcohol
  5. customthen dried

Sources & evidence

ORD record
ord-179732200bd94c90b823eeac5dfa5191
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

Loading…