Sodium Hydroxide → [4-(2,2,4,4-Tetramethyl-chroman-6-yl-ethynyl)phenyl]acetic Acid

HRID 2299353Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of [4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)phenyl] acetic acid methyl ester (Compound 27, 0.047 g, 0.13 mmol) in 5 mL of methanol was treated with 1M sodium hydroxide solution (2 mL) and heated at 55° C. for 2 h. The volatiles were distilled off in vacuo and the residue was acidified with 10% hydrochloric acid and extracted with ethyl acetate (×2). The combined organic phase was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was purified by preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase to afford the title compound (0.034 g, 82%). 1H NMR (300 MHz, CDCl3): δ 7.49-7.45 (m, 3H), 7.26-7.22 (m, 3H), 6.75 (d, 1H, J=8.2 Hz), 3.65 (s, 2H), 1.84 (s, 2H), 1.36 (s, 6H), 1.35 (s, 6H).

Workup

distillationThe volatiles were distilled off in vacuo
extractionextracted with ethyl acetate (×2)
washThe combined organic phase was washed with brine (×1)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated in vacuo to a residue which
customwas purified by preparative reverse phase

Sources & evidence

ORD record: ord-096436aa9e7142c2a992e04caff8c75a
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495552B2

Reaction notes

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