Water → NSC305212

HRID 1270449Notes

Reaction equation

HRID 1270449 reaction equation
[CH2:1]1[C@@H:3](N)[C@@H:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-:11].[K+].[OH2:13]>C(O)CO>[C:5]1([C:2]2([CH2:3][C:1]([OH:13])=[O:11])[CH2:6][CH2:5][CH2:2][CH2:1][CH2:3]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 19493(1R,2S)-Tranylcypromine

Product 1

HCID 327959NSC305212Yield 88%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Compound 1 (3.58 g, 17.96 mmol) and KOH (4.42 g, 78.77 mmol) in ethylene glycol (35 mL) was heated at 170° C. for 48 h then cooled to rt. The reaction mixture was diluted with H2O then extracted with Et2O (2×). The aqueous phase was acidified with 6N HCl then extracted with Et2O (3×) and dried over anhydrous sodium sulfate to give (1-phenyl-cyclohexyl)-acetic acid (3.43 mg, 88%) as a tan solid. Mass Spec [M+H]+=219.1.

Workup

  1. extractionthen extracted with Et2O (2×)
  2. extractionthen extracted with Et2O (3×)
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a8ce11111af24ce185f894f134e57f9e
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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