Trimethyl orthoformate → (E)-3-(4-dimethoxymethylphenyl)acrylic Acid

HRID 735167Notes

Reaction equation

CO[CH:3]([O:6][CH3:7])[O:4][CH3:5].C([C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1)=O>CO>[CH3:7][O:6][CH:3]([O:4][CH3:5])[C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

38.81 mL (0.354 mmol) of trimethylorthoformate is added to a suspension of 25 g (0.141 mol) of (E)-3-(4-formylphenyl)acrylic acid in 350 mL of methanol and the mixture is refluxed for 48 hours. After cooling, the reaction mixture is filtered and the filtrate is evaporated down. The residue is taken up in 500 mL of dichloromethane and filtered through CELITE® filter aid. The filtrate is evaporated down to 150 mL and cooled to 0° C. The precipitate formed is filtered off, washed with dichloromethane/petroleum ether (1:1), and dried at 60° C. in the circulating air dryer. Yield: 12.05 g (31.5% of theory); C12H14O4 (M=222.24); calc.: molecular ion peak (M+H)+: 245; found: molecular ion peak (M+H)+: 245; Rf value: 0.6 (silica gel, petroleum ether/ethyl acetate (1:1)).

Workup

temperaturethe mixture is refluxed for 48 hours
temperatureAfter cooling
filtrationthe reaction mixture is filtered
customthe filtrate is evaporated down
filtrationfiltered through CELITE®
filtrationfilter aid
customThe filtrate is evaporated down to 150 mL
customThe precipitate formed
filtrationis filtered off
washwashed with dichloromethane/petroleum ether (1:1)
customdried at 60° C. in the circulating air dryer

Sources & evidence

ORD record: ord-f9f61fd29a084fca98b6c052164dbe89
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592373B2

Reaction notes

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