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

HRID 51716Notes

Reaction equation

HRID 51716 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][CH:9]=2)[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][CH:9]=2)[CH2:6][CH2:7]1)([CH3:3])[CH3:2]

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 ethyl 4-[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-fd4798a600f04504964aa61a1ccfbe65
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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