Potassium Hydroxide → 3(R)-hydroxy-2-methylene-3-phenylpropanoic Acid

HRID 1007585Notes

Reaction equation

HRID 1007585 reaction equation
[OH-].[K+].[OH:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[CH2:10])[C:6]([O:8]C)=[O:7]>O.CO>[OH:3][C@H:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[CH2:10])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

Product 1

HCID 120136653(R)-hydroxy-2-methylene-3-phenylpropanoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (2.65 g, 0.047 mol, 1.3 eq) in water (60 mL) was added drop wise to a solution of 1b (7 g, 0.036 mol, 1 eq) in methanol (20 mL) (see FIG. 5). The mixture was stirred at room temperature for 15 h. The solution was then concentrated under vacuum. The aqueous phase was washed with ether (2×100 mL), acidified with 6N aqueous HCl solution and extracted with ether (3×100 mL). The combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate. Evaporation of the solvent afforded a colorless oil which crystallized upon standing. The desired product 9b was obtained as a solid (6.29 g, 97%). Rf 0.26 (hexane/EtOAc=6:4). 1H NMR δ (DMSO-d6) 5.41 (s, 1H), 5.61 (s, 1H), 5.93 (s, 1H), 6.15 (s, 1H), 7.22 (m, 5H), 12.45 (s, 1H). [M−H]− 177.1, tR=1.23 min; purity: 91%.

Workup

  1. concentrationThe solution was then concentrated under vacuum
  2. washThe aqueous phase was washed with ether (2×100 mL)
  3. extractionextracted with ether (3×100 mL)
  4. washThe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent
  7. customafforded a colorless oil which
  8. customcrystallized

Sources & evidence

ORD record
ord-73242561a24f4c5daf7d6c22eac5d180
Source dataset
uspto-grants-2004_09
Patent number
US06794510B2

Reaction notes

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