Lithium hydroxide, monohydrate → 2-Cyclohexylpropionic acid

HRID 449425Notes

Reaction equation

HRID 449425 reaction equation
[CH:1]1([CH:7]([CH3:12])[C:8]([O:10]C)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>CO.O>[CH:1]1([CH:7]([CH3:12])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Conditions

Temperature
60 °C

Procedure

A reaction mixture of methyl 2-cyclohexylpropanoate (0.30 g, 1.8 mmol) and lithium hydroxide monohydrate (0.12 g, 2.8 mmol) in methanol (3.0 mL) and water (1.0 mL) was stirred at 60° C. for 2 h. The mixture was concentrated to remove methanol, washed with ether to remove some impurity, then adjusted to pH=2 with 1 N HCl (aqueous). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford the crude product which was directly used for next step without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove methanol
  3. washwashed with ether
  4. customto remove some impurity
  5. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7261de6015e34e7c8be81f05839b39a1
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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