Methanol → (3R)-3-(4-Chlorophenyl)-3-cyclopropylpropanoic Acid

HRID 1835033Notes

Reaction equation

HRID 1835033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:12]2[CH2:14][CH2:13]2)[CH2:9][C:10]#N)=[CH:4][CH:3]=1.[OH-:15].[Na+].C[OH:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:12]2[CH2:14][CH2:13]2)[CH2:9][C:10]([OH:18])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 60104338(3R)-3-(4-chlorophenyl)-3-cyclopropylpropanenitrile

Product 1

HCID 42073399(3R)-3-(4-Chlorophenyl)-3-cyclopropylpropanoic AcidYield 100%

Conditions

Temperature
0 °C

Procedure

(3R)-3-(4-Chlorophenyl)-3-cyclopropylpropanenitrile (5.30 g, 25.8 mmol) is refluxed for 18 hours in a mixture of methanol (100 ml) and a 10% aqueous sodium hydroxide (100 ml). Methanol is removed in vacuo, the residual solution is cooled to 0° C. and acidified to pH 4 with concentrated hydrochloric acid. The aqueous layer is extracted with ethyl acetate (100 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a colorless liquid (5.79 g, 100%) which is characterized by 1HNMR, IR and mass spectral analysis and used without further purification.

Workup

  1. customMethanol is removed in vacuo
  2. extractionThe aqueous layer is extracted with ethyl acetate (100 ml)
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c45b67a12414e509ee98ef033066cde
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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