Hydrochloric Acid → Methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Methyl Acrylate	HCID 7294	—
Reactant	4-Aminophenethyl alcohol	HCID 66904	—
Reactant	Sodium Nitrite	HCID 23668193	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Acetone	HCID 180	—
Solvent	Water	HCID 962	—
Product	Methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate	HCID 86600802	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

2-(4-Aminophenyl)ethanol (11 g, 81 mmol) and 32 ml conc HCl was dissolved in acetone and cooled to 0° C. Sodium nitrite (5.6 g, 81 mmol) in 20 ml water was added dropwise. The temperature was kept under 0° C. After one hour, methyl acrylate (70 g, 808 mmol) and CuI (1.6 g, 8 mmol) were added (<0° C.). The reaction mixture was stirred at room temperature overnight.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07276539B2
Source dataset	uspto-grants-2007_10
ORD ID	ord-1c9e5fe183944f61a4850dedfa5753dd
Source note	uspto-grants-2007_10