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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1626488Generated: October 30, 2026

Trifluoroacetic acid → 4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

https://huagongshe.com/reaction/1626488

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantEthyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylateHCID 67080248—
SolventDichloromethaneHCID 6344—
Product4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidHCID 5824439597%

Reaction Steps

Ethyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate (8.62 g, 19.91 mmol) was diluted with DCM (40 ml) followed by the portion wise addition of TFA (30 ml). After stirring for 1 hour, the reaction was concentrated and placed under vacuum over the weekend. The residue was taken up in DCM and washed with saturated bicarbonate and 1N HCl. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to yield the desired compound (7.278 g, 19.32 mmol, 97.00% yield) as a nice white foam.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08785445B2
Source datasetuspto-grants-2014_07
ORD IDord-90b37ead0ea343d5996ceacd6d352c4b
Source noteuspto-grants-2014_07