Hydrochloric Acid → 3-Chloro-2-methoxyphenol

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	2,6-Dichloroanisole	HCID 16127	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	3-Chloro-2-methoxyphenol	HCID 157004	62%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A reaction mixture of 1,3-dichloro-2-methoxybenzene (885 mg, 5 mmol), potassium hydroxide (280 mg, 5 mmol), tris(dibenzylideneacetone)dipalladium (115 mg, 0.125 mmol) and tert-butyl X-Phos (159 mg, 0.375 mmol) in dioxane/water (1:1, 5 mL) was stirred at 100° C. for 2 hours. The reaction mixture was mixed with aqueous hydrochloride solution (1 N). The organic components were extracted with EtOAc. The combined EtOAc layers were washed with brine, and then concentrated. The residue was purified by chromatography. Elution with 10% EtOAc in hexane gave 3-chloro-2-methoxyphenol (22-1, 489 mg, 62% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 6.98-6.84 (m, 3H), 5.73 (br s, 1H), 3.93 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815875B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-a2977d6aac52496693eb85aca0f7dc6e
Source note	uspto-grants-2014_08