Potassium Hydroxide → 2-[4-(8-Hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-propionic acid

HRID 1765728Notes

Reaction equation

C[O:2][C:3](=[O:29])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([OH:24])[CH:23]=2)[O:20][C:19]([CH3:26])([CH3:25])[CH2:18][C:17]3([CH3:28])[CH3:27])=[CH:8][CH:7]=1)[CH3:5].[OH-].[K+]>CO.O1CCCC1>[OH:24][C:22]1[CH:23]=[C:14]([C:13]#[C:12][C:9]2[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:29])=[O:2])=[CH:7][CH:8]=2)[CH:15]=[C:16]2[C:21]=1[O:20][C:19]([CH3:26])([CH3:25])[CH2:18][C:17]2([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-[4-(8-hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-propionic acid methyl ester (Intermediate 22, 0.018 g, 0.046 mmol) in methanol (1 mL) and tetrahydrofuran (0.5 mL) was treated with a 2M solution of potassium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at 80° C. for 2 h. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over-anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (0.017 g, 100%).

Workup

customthe resulting reaction mixture
customThe volatiles were evaporated in vacuo to a residue that
extractionextracted with ethyl acetate
washThe organic phase was washed with water and brine, and dried over-anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-f9bb95fa95e3463cbafd6966eb52edd6
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226951B2

Reaction notes

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