Lithium hydroxide, monohydrate → HCID 54302611, compound

HRID 636013Notes

Reaction equation

HRID 636013 reaction equation
[CH:1]1([CH2:7][C@H:8]([C@H:13]([OH:17])[CH2:14][CH2:15][CH3:16])[C:9]([O:11]C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>C1COCC1.CO.O>[CH:1]1([CH2:7][C@H:8]([C@H:13]([OH:17])[CH2:14][CH2:15][CH3:16])[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11128482HCID 11128482, compound

Product 1

HCID 54302611HCID 54302611, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

Methyl (2R,3R)-2-cyclohexylmethyl-3-hydroxyhexanoate (3.44 g, 14.2 mmol) is dissolved in 3:1:1 THF-MeOH-H2O (35 mL). To this is added lithium hydroxide monohydrate (1.79 g, 42.6 mmol). The reaction mixture is stirred for 18 h at 25° C. and the mixture is then extracted with ether. The aqueous layer is acidified with solid sodium bisulfate and then extracted with two 250-mL portions of ether. The combined organics are washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure to afford (2R,3R)-2-cyclohexylmethyl-3-hydroxyhexanoic acid as a solid (3.05 g, 96% yield).

Workup

  1. extractionthe mixture is then extracted with ether
  2. extractionextracted with two 250-mL portions of ether
  3. washThe combined organics are washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c057d499ea84c608fc07e2c43e3bccf
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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