Sodium Hydroxide → (S)-3-benzyloxymethyloxy-2-methylpropionic acid

HRID 654991Notes

Reaction equation

HRID 654991 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@H:12]([CH3:17])[C:13]([O:15]C)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@H:12]([CH3:17])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14348497methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

Product 1

HCID 14348499(S)-3-benzyloxymethyloxy-2-methylpropionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (S)-3-benzyloxymethyloxy-2-methylpropionate (1.20 g; 5 mmole) was dissolved in methanol (12 ml), and a lN sodium hydroxide solution (5.5 ml) was added thereto with ice-cooling, followed by stirring at room temperature for overnight. The reaction mixture was diluted with water (30 ml) and washed with ether (20 ml) two times. The aqueous layer was acidified with 6N hydrochloric acid with ice-cooling and extracted with ethyl acetate (30 ml) three times. The extracts were combined together, washed with water and dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (S)-3-benzyloxymethyloxy-2-methylpropionic acid.

Workup

  1. temperaturewith ice-cooling
  2. washwashed with ether (20 ml) two times
  3. temperaturecooling
  4. extractionextracted with ethyl acetate (30 ml) three times
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffeef2f695554ddfb9bdfc29635e1d2d
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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