Benzyl Alcohol → D-leucic acid benzyl ester

HRID 1769443Notes

Reaction equation

HRID 1769443 reaction equation
[OH:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[OH:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 439960(R)-2-hydroxy-4-methylpentanoic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 9991100D-leucic acid benzyl esterYield 66.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.05 g of 2-(R)-hydroxy-4-methylpentanoic acid, 2.01 g of benzyl alcohol and 0.251 g of p-toluenesulfonic acid monohydrate in 40 ml of benzene was heated to reflux for 1.5 hours. The reaction mixture, after being allowed to cool, was washed with a saturated aqueous solution of sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate. Then the solvent was distilled off under reduced pressure to yield the title compound as a colorless oil (2.30 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. washwas washed with a saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-33eacbde931f45b59e8bcaa96e86d4e0
Source dataset
uspto-grants-1995_01
Patent number
US05380921

Reaction notes

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