Dimethyl Sulfate → Methyl 2-chloro-4-methoxybenzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfate	HCID 6497	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	2-Chloro-4-hydroxy-benzoic acid methyl ester	HCID 13498830	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 2-chloro-4-methoxybenzoate	HCID 13498831	—

Reaction Conditions

Temperature	62.5 °C

Reaction Steps

To a solution of compound of example 163 (2.8 g, 15 mmol) in dry dioxane (50 mL) was added NaH (50%, 1.44 g, 30 mmol) and dimethyl sulfate (3.78 g, 30 mmol). It was stirred at 60-65° C. for 1 h. It was poured into ice water and extracted with EtOAc (2×100 mL). The organic extract was washed with brine, dried (anhydrous Na2SO4) and concentrated to obtain the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07884127B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-9137fee05f894d7990cfd4273956aa17
Source note	uspto-grants-2011_02