Methanol → (R)-methyl 2-hydroxydecanoate

HRID 1440509Notes

Reaction equation

HRID 1440509 reaction equation
[OH-].[Na+].[OH:3][CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([O:7][CH3:8])=[O:6].CO>O>[CH3:8][O:7][C:5](=[O:6])[C@H:4]([OH:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 549544Methyl 2-hydroxydecanoate

Product 1

HCID 10465463(R)-methyl 2-hydroxydecanoateYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lipase P-30 (Amano from Pseudomonas fluorescens) (1 g, 5% by weight) was dissolved in 140 ml of H2O and the pH of the solution adjusted to 7.5 with a 1N solution of NaOH. Racemic methyl 2-hydroxydecanoate (20.12 g, 0.995 mol) (CP-112,994) was added to the enzyme solution and the pH controlled to maintain a range of 6-8. The reaction was stirred at room temperature for 10 hours (total of 46.5 mL of 1N NaOH added) and worked up by addition of 140 ml of methanol. The aqueous alcohol was extracted with hexane (3×200 mL). The hexane extracts were combined and dried (MgSO4). Following concentration, the desired (R)-methyl-2-hyroxydecanoate (10.08 g, 0.049 mol, 50%) was obtained: [α]D =-3.1° (c=1, MeOH). The aqueous extracts were acidified to pH 1-2 with HCl and extracted with two portions of ethyl acetate (200 mL). The combined extracts were dried (MgSO4) and concentrated to give (S)-2-hydroxydecanoic acid (8.91 g, 0.047 mol, 47%): mp 70°-72°; [α]D =-1.7° (c=1, MeOH).

Workup

  1. temperatureto maintain a range of 6-8
  2. extractionThe aqueous alcohol was extracted with hexane (3×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentration

Sources & evidence

ORD record
ord-03ca8e2711fd4bd4b3ae9dddbd96b9f1
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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