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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1161099Generated: October 29, 2026

Diazomethane → 1-(3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanone

https://huagongshe.com/reaction/1161099

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiazomethaneHCID 9550—
ReactantOxalyl chlorideHCID 65578—
Reactant3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acidHCID 57884471—
CatalystDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Product1-(3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanoneHCID 86620599100%

Reaction Steps

Add oxalyl chloride (256 mg, 2.02 mmol) to a solution of 3-{[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid (0.786 mg, 1.84 mmol) in tetrahydrofuran (0.20M). Add dimethylformamide (5 drops). Add ethereal solution of diazomethane (1.90 mmol) and stir for 2 hours. Add hydrochloric acid (4N in dioxane) to quench unreacted diazomethane and evaporate solvents to afford the title compound (0.786 mg, 1.84 mmol, 94%): MS (m/z): 457 (M−H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07816523B2
Source datasetuspto-grants-2010_10
ORD IDord-42d03f24d80a41059693be64caab0228
Source noteuspto-grants-2010_10