Sodium Hydroxide → 4-[4-(1-Isopropoxycyclopropyl)-phenylethynyl]-benzoic Acid

HRID 381081Notes

Reaction equation

HRID 381081 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([O:22][CH:23]([CH3:25])[CH3:24])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH:23]([O:22][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:26])=[O:3])=[CH:10][CH:9]=3)=[CH:14][CH:15]=2)[CH2:20][CH2:21]1)([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568976Ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 102679914-[4-(1-Isopropoxycyclopropyl)-phenylethynyl]-benzoic AcidYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate (Compound 71, 110.0 mg, 0.32 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (120.0 mg, 3.0 mmols, 3.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 89.0 mg (88%) of the title compound as a yellow solid.

Sources & evidence

ORD record
ord-6bf8cd29fecf4223846efeb3a85e454c
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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