Glycerol → Solketal

Participants

Reaction Steps

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.

Provenance & Evidence