Methanol → DL-2-(4-chlorophenyl)propanoic acid

HRID 1971575Notes

Reaction equation

HRID 1971575 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:15])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:7].CO>O1CCCC1.O>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH:6]([CH3:7])[C:5]([OH:15])=[O:4])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 12398854Methyl 2-(4-chlorophenyl)propanoate

Product 1

HCID 102525DL-2-(4-chlorophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.17 g, 7.10 mmol) was added to a stirred solution of 2-(4-chloro-phenyl)-propionic acid methyl ester (0.47 g, 2.366 mmol) in tetrahydrofuran, water and:methanol (4:1:1, 12 ml). The mixture was stirred overnight and the volatiles evaporated in vacuo. The mixture was basified by addition of aqueous sodium hydrogencarbonate and washed with ethyl acetate. The aqueous was then acidified with 2M HCl and the product extracted into ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired product. Yield 0.4 g, 91%. NMR 1H (300 MHz, DMSO): 1.36 (d, 3H), 3.72 (q, 1H), 7.23-7.38 (m, 4ArH), 12.48 (bs, 1H).

Workup

  1. customthe volatiles evaporated in vacuo
  2. additionThe mixture was basified by addition of aqueous sodium hydrogencarbonate
  3. washwashed with ethyl acetate
  4. extractionthe product extracted into ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74260de340c848f8b506846372a69f3e
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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