Glycerol → 3-(Benzyloxy)-1,2-propanediol

As an alternative procedure to a stirred solution of the protected glycerol (6.7 g, 0.05 mole) in dry THF (100 mL) was added NaH (1.8 g, 0.075 mole) portionwise at 0° C. The reaction mixture was refluxed for 1.5 h, and benzyl bromide (10.3 g, 0.06 mole) was added. The mixture was stirred at room temperature. Once the reaction was completed, 2 mL of methanol was added at 0° C. to destroy the excess of NaH. The reaction mixture was extracted with 3×50 mL of ethyl ether, and the combined ether layers dried over sodium sulfate. After solvent removal, the residue of (11.9 g, Y=61%). was combined with 60 mL of 10% acetic acid, then heated (oil bath, 100° C.), until the original emulsion disappeared (about 0.5 h), After concentration, the residue was distilled in vacuo, giving 8.1 g (b.p.116-118° C./50μ) (Y=89%).

1. temperatureThe reaction mixture was refluxed for 1.5 h
2. customto destroy the excess of NaH
3. extractionThe reaction mixture was extracted with 3×50 mL of ethyl ether
4. dry with materialthe combined ether layers dried over sodium sulfate
5. customAfter solvent removal
6. temperatureheated (oil bath, 100° C.)
7. custom(about 0.5 h)
8. concentrationAfter concentration
9. distillationthe residue was distilled in vacuo
10. customgiving 8.1 g (b.p.116-118° C./50μ) (Y=89%)

ORD record

ord-4a0ce279e2134307aa47bc45be97e65d

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441214B1