Sodium Hydroxide → HCID 22012326, compound

HRID 1533268Notes

Reaction equation

HRID 1533268 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[OH:17])[C:11]([O:13]CC)=[O:12])=[CH:4][C:3]=2[O:2]1.[OH-].[Na+]>C(O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[OH:17])[C:11]([OH:13])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54379492HCID 54379492, compound

Product 1

HCID 22012326HCID 22012326, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionate (4.2 g) in ethanol (50 ml) was added 1M sodium hydroxide solution (26.2 ml) at room temperature. After being stirred for 1.5 hours at the same temperature, the mixture was concentrated in vacuo. The residue was dissolved in 1N hydrochloric acid (50 ml) and ethyl acetate (100 ml) and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized from n-hexane to give (2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionic acid (1.43 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1N hydrochloric acid (50 ml)
  3. washethyl acetate (100 ml) and the organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-c98e5f704a2d4bfb96828e366b59e286
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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