Benzyl Alcohol → Malic Acid

HRID 981757Notes

Reaction equation

HRID 981757 reaction equation
[C:1]([OH:9])(=[O:8])[C@@H:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].C1(N=C=NC2CCCCC2)CCCCC1.C(O)C1C=CC=CC=1>O1CCCC1>[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 92824D-Malic acid

Product 1

HCID 525Malic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an example of the process wherein the cyclic anhydride is formed with a diimide, D-malic acid is dissolved in tetrahydrofuran and 1.1 molar equivalents of dicyclohexylcarbodiimide are added to the solution. The reaction mixture is stirred for about an hour and is then filtered to remove the precipitate of dicyclohexylurea. An excess (ca. 1.5 to 2.0 equiv.) of benzyl alcohol is added to the filtrate containing the malic acid cyclic anhydride and the solution is stirred for about 6 to about 12 hours. The reaction mixture is evaporated and the impure monobenzyl malate is dissolved in a water immiscible solvent such as ethyl acetate. The product is extracted with a base such as aqueous sodium bicarbonate, and after acidification of the extract the ester is extracted with ethyl acetate or other suitable solvent. The extract is dried and evaporated to yield the monobenzyl ester of malic acid represented by the formula ##STR51##

Workup

  1. filtrationis then filtered
  2. customto remove the precipitate of dicyclohexylurea
  3. stirringthe solution is stirred for about 6 to about 12 hours
  4. customThe reaction mixture is evaporated
  5. dissolutionthe impure monobenzyl malate is dissolved in a water immiscible solvent such as ethyl acetate
  6. extractionThe product is extracted with a base such as aqueous sodium bicarbonate
  7. extractionafter acidification of the extract the ester
  8. extractionis extracted with ethyl acetate or other suitable solvent
  9. customThe extract is dried
  10. customevaporated

Sources & evidence

ORD record
ord-207c9612f77b49cd8c54dddaf7c7bf62
Source dataset
uspto-grants-1991_02
Patent number
US04992544

Reaction notes

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