Glycerol → Solketal

HRID 1024592Notes

Reaction equation

HRID 1024592 reaction equation
O[CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH3:7][C:8]1([CH3:15])[O:12][CH:11]([CH2:13][OH:14])[CH2:10][O:9]1.S(C1C=CC(C)=CC=1)(OC)(=O)=O.[OH-:28].[Na+]>O.CC(C)=O>[CH3:2][C:3]([CH2:5][OH:6])([OH:4])[C:8]([CH3:15])([CH3:7])[OH:28].[CH3:7][C:8]1([CH3:15])[O:12][CH:11]([CH2:13][OH:14])[CH2:10][O:9]1

Participants

8

Reactant 4

HCID 753Glycerol2×HCID 6645Methyl p-toluenesulfonateHCID 7528Solketal2×HCID 14798Sodium Hydroxide

Product 2

HCID 7528SolketalHCID 126036792,3-Dimethylbutane-1,2,3-triol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Trimethyl glycerol was prepared from glycerol through a ketal glecerol derivative, solketal (1,2-isopropylidene glycerol) as shown in FIG. 2. Solketal starting material was prepared by reacting 1 g glycerol with 2 ml acetone and 1 g Dowex 50W strong cation exchange resin (Dow Chemical Co., Midland, Mich.) at 60° C. for 1 hour. The resultant solketal (3 mmol) was reacted with 3 mmol methyl tosylate (as prepared in Example 1) in 3 mmol NaOH with mL water in a small scale vessel for 2 hours at 70° C., producing methyl solketal. Hydrolysis of the methyl solketal was effected by reaction with Dowex 50W strong cation exchange resin (½″) in 4 ml methanol for 2 hours at 70° C., producing 1-methyl glycerol. The 1-methyl glycerol produced from the hydrolysis was reacted with 2 molar equivalents of methyl tosylate in aqueous NaOH for 2 hours at 70° C., yielding 1,2,3-trimethoxy glycerol ether.

Workup

  1. customat 60° C.
  2. customfor 1 hour

Sources & evidence

ORD record
ord-5b1f13767fe94c68a04b3af4cfd0e8ae
Source dataset
uspto-grants-2014_05
Patent number
US08722943B1

Reaction notes

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