Potassium Hydroxide → HCID 86699750, compound

HRID 515181Notes

Reaction equation

HRID 515181 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[CH:18]1[CH2:20][CH2:19]1)C.[OH-].[K+]>C(O)CO.O>[CH:18]1([C:6]2[CH:7]=[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:9]=[C:10]([CH3:11])[C:5]=2[C:4]([OH:21])=[O:3])[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86699748HCID 86699748, compound

Product 1

HCID 86699750HCID 86699750, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

To a stirred solution of 2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzoic acid ethyl ester (0.54 g, 1.86 mmol) in ethylene glycol (10 ml) is added solid potassium hydroxide (0.42 g, 7.47 mmol) and the mixture is stirred at 150-160° C. for 16 h. After completion of the reaction, the mixture is diluted with water (30 ml) and extracted with ethyl acetate (2×10 ml). The aqueous layer is acidified with 2M HCl to pH 3 and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (3×40 ml), dried over sodium sulfate and concentrated in vacuo yielding 2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzoic acid (0.34 g, 1.3 mmol, 70%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe combined organic layers are washed with water (3×40 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2194b3cf0bcd44a9aa1730d0f61af0dc
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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