Acetaldehyde → 1-(2-Chloro-4-methoxy-phenyl)-ethanol

Participants

Role	Name	HCID	Charge
Reactant	Acetaldehyde	HCID 177	—
Reactant	Water	HCID 962	—
Reactant	1-Bromo-2-chloro-4-methoxybenzene	HCID 2756863	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Hexane	HCID 8058	—
Product	1-(2-Chloro-4-methoxy-phenyl)-ethanol	HCID 21755593	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

A 1.6M solution of n-butyllithium in hexane (4 ml) was added to a solution of 4-bromo-3-chloroanisole (CAS Reg. No. 50638-46-5, 1.3 g) in THF (20 ml) at −78° C. The mixture was stirred for 30 min at −78° C. Acetaldehyde (0.7 ml) was added to the mixture. The mixture was allowed to warm to room temperature. Water (50 ml) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil to give the title compound (983 mg) as colorless oil. MS (m/e)=186 [M+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268820B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-17758e9202a64c38a19add3502df54d7
Source note	uspto-grants-2012_09