Acetone → 2-Hydroxyisobutyric acid

HRID 1370159

Reaction equation

HRID 1370159 reaction equation
[CH3:1][C:2]([CH3:6])([OH:5])[C:3]#[N:4].C(O)(=[O:10])CC.CC(C)=O.[OH:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[OH:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19].[OH:5][C:2]([CH3:6])([CH3:1])[C:3]([NH2:4])=[O:10]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 1032Propionic AcidHCID 6406Acetone Cyanohydrin3×HCID 116712-Hydroxyisobutyric acid

Product 2

HCID 116712-Hydroxyisobutyric acidHCID 83059Propanamide, 2-hydroxy-2-methyl-

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

A suspension of 0.343 g (wet cell paste) Comamonas testosteroni 22-1 cells (ATCC PTA-1853) in 5.61 mL of 50 mM potassium phosphate buffer (pH 6.0) was placed into a 15-mL polypropylene centrifuge tube, then 51.0 mg of acetone cyanohydrin (0.10 M final concentration of acetone cyanohydrin in the suspension) was added and the resulting suspension mixed on a rotating platform at 25° C. Samples for analysis (0.180 mL) were mixed with 0.020 mL of 1.0 M propionic acid (HPLC external standard), centrifuged, and the supernatant analyzed by HPLC for acetone cyanohydrin, acetone, and 2-hydroxyisobutyric acid. After 21 h, the yields of 2-hydroxyisobutyric acid, 2-hydroxyisobutyramide, and acetone were 40.4%, 0%, and 34.5%, respectively, with 18.4% acetone cyanohydrin remaining.

Workup

  1. customwas placed into a 15-mL polypropylene centrifuge tube
  2. additionthe resulting suspension mixed on a rotating platform at 25° C

Sources & evidence

ORD record
ord-c9484660797e43168e8e6483ade7e481
Source dataset
uspto-grants-2003_06
Patent number
US06582943B1

Linked notes

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