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

HRID 1885473Notes

Reaction equation

HRID 1885473 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 IN 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-3097d4385e7c44c2ae271d70b179fa21
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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