Benzyl Alcohol → HCID 11075036, compound

To a solution of D-malic acid (18.8 g., 140.2 mmole) in 150 ml. of freshly-distilled THF was added dicyclohexylcarbodiimide (DCC, 1.1 equiv.) and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was filtered to remove the precipitate of dicyclohexylurea which formed. The precipitate was washed with two 50 ml. portions of THF and the washings were combined with the filtrate. To the combined filtrate and washings were added two equivalents of benzyl alcohol and the solution was stirred overnight at room temperature. The reaction mixture was evaporated to remove the solvent and the residual oil containing the monoester was dissolved in 100 ml. of ethyl acetate. The solution was extracted with three 50 ml. portions of a 10% solution of sodium carbonate in water and the extracts were combined, acidified to pH 2 and extracted with three 50 ml. portions of ethyl acetate. The extracts were combined, washed with 25 ml. of brine, dried over magnesium sulfate, filtered, and then evaporated to dryness to yield D-malic acid monobenzyl ester as an oil in 64% yield.

1. filtrationThe reaction mixture was filtered
2. customto remove the precipitate of dicyclohexylurea which
3. customformed
4. washThe precipitate was washed with two 50 ml
5. stirringthe solution was stirred overnight at room temperature
6. customThe reaction mixture was evaporated
7. customto remove the solvent
8. additionthe residual oil containing the monoester
9. dissolutionwas dissolved in 100 ml
10. extractionThe solution was extracted with three 50 ml
11. extractionextracted with three 50 ml
12. washwashed with 25 ml
13. dry with materialof brine, dried over magnesium sulfate
14. filtrationfiltered
15. customevaporated to dryness

ORD record

ord-d06dca65fe084fdd887a43e79a081a94

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04992544