Sodium Hydroxide → 4-[4-(1-Isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoic acid

HRID 24167Notes

Reaction equation

HRID 24167 reaction equation
[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)=[CH:10][C:9]=2[CH3:27])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O1CCCC1>[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)=[CH:10][C:9]=2[CH3:27])[CH2:6][CH2:7]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568844Ethyl4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate2×

Product 1

HCID 99674874-[4-(1-Isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoic acidYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate (Compound 83, 60.0 mg, 0.17 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 38.0 mg (69%) of the title compound as a colorless solid.

Sources & evidence

ORD record
ord-789b75903f614f679e6c47dfea6ce2df
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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