Hydrochloric Acid → (R)-(-)-Methyl mandelate

(R)-Mandelic acid (2.568 g, 16.87 mmol) and 2,2-dimethoxypropane (5.1 mL, 41.48 mmol) were dissolved in MeOH (100 mL) and 12M HCl (100 mL) was added. The resulting solution was stirred for 20 hr under a CaCl2 tube and evaporated to dryness under reduced pressure. EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL) were added, and the aqueous phase was extracted with EtOAc (3×100 mL). The organic fractions were dried with MgSO4, and evaporated under reduced pressure to give (R)-methyl mandelate, (R)-4, quantitatively (2.78 g) as a white solid which was of sufficient purity for the next step.

1. customevaporated to dryness under reduced pressure
2. additionEtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL) were added
3. extractionthe aqueous phase was extracted with EtOAc (3×100 mL)
4. dry with materialThe organic fractions were dried with MgSO4
5. customevaporated under reduced pressure

ORD record

ord-f0f3852e6d334da699a657b3325866f7

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357524B2