Methanol → (R)-(-)-Methyl mandelate

HRID 1080700Notes

Reaction equation

HRID 1080700 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].S(=O)(=O)(O)O.[CH3:17]O>>[C:1]([O:11][CH3:17])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 11914(-)-Mandelic acid

Product 1

HCID 2724623(R)-(-)-Methyl mandelate

Procedure

To a stirred solution of D-(-)-mandelic acid (20 g) in methanol (100 ml) was added concentrated sulfuric acid (6 g) and the mixture was refluxed for 2.5 hours. After cooling to room temperature it was concentrated to about 50 ml and the residue was dissolved in methylene chloride (about 300 ml). The solution was the washed with water, saturated sodium bicarbonte and water, dried (magnesium sulfate) and evaporated to give a clear oil, which crystallized upon cooling to give 21.7 g of methyl D-(-)-mandelate, a compound of Formula 6, wherein R5 is phenyl.

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. concentrationwas concentrated to about 50 ml
  3. dissolutionthe residue was dissolved in methylene chloride (about 300 ml)
  4. washwashed with water, saturated sodium bicarbonte and water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customto give a clear oil, which
  8. customcrystallized
  9. temperatureupon cooling

Sources & evidence

ORD record
ord-d5bb181c77b5477988f60541a40e5d99
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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