Isopropyl Acetate → (2R)-2-(hydroxymethyl)hexanoic Acid

HRID 271975Notes

Reaction equation

HRID 271975 reaction equation
C[C@@H]([NH3+])C1C=CC=CC=1.[CH2:10]([C@H:14]([CH2:18][OH:19])[C:15]([O-:17])=[O:16])[CH2:11][CH2:12][CH3:13].C(OC(C)C)(=O)C>Cl>[CH2:10]([C@H:14]([CH2:18][OH:19])[C:15]([OH:17])=[O:16])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 7915Isopropyl AcetateHCID 131727187(r)-2-Butyl-3-hydroxypropionic acid (r)-alpha-methylbenzylammonium salt

Product 1

HCID 11550035(2R)-2-(hydroxymethyl)hexanoic AcidYield 98.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(R)-2-Butyl-3-hydroxypropionic acid (R)-α-methylbenzylammonium salt (5, 10.0 g) is dissolved in 2 N HCl (40.0 mL) and isopropyl acetate (50.0 mL) is added to the mixture. After mixing for 5 min, the organic layer is separated and the aqueous layer is extracted with isopropyl acetate (3×50.0 mL). The combined organic layers are washed with water (20.0 mL) and concentrated under vacuum (20 mbar) until no further solvent distills to afford (R)-2-butyl-3-hydroxypropionic acid (1, 5.4 g, 98%); oil; [α]D+6.5 (c=1.0, CH3OH), (R):(S)=99.3:0.7.

Workup

  1. additionAfter mixing for 5 min
  2. customthe organic layer is separated
  3. extractionthe aqueous layer is extracted with isopropyl acetate (3×50.0 mL)
  4. washThe combined organic layers are washed with water (20.0 mL)
  5. concentrationconcentrated under vacuum (20 mbar) until no further solvent
  6. distillationdistills

Sources & evidence

ORD record
ord-9645ef5267364df880496af826ae6058
Source dataset
uspto-grants-2008_11
Patent number
US07452999B2

Reaction notes

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