Acetone → Methyl 7-[[5-(4-acetyl-3-methoxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Acetone	HCID 180	—
Reactant	Dimethyl Sulfate	HCID 6497	—
Reactant	2-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman	HCID 13537870	—
Solvent	Potassium Hydroxide	HCID 14797	—
Product	Methyl 7-[[5-(4-acetyl-3-methoxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate	HCID 14722866	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

Methyl 7-[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]oxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate (1 mMol), prepared as described in U.S. Pat. No. 4,565,882, was dissolved in acetone containing 2.5 equivalents of potassium hydroxide and 3 equivalents of dimethyl sulfate. The mixture was heated at 40° C. for 10 hours and then cooled; the solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was separated and dried over magnesium sulfate. Evaporation of the volatiles in vacuo afforded the methyl ether.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04889871
Source dataset	uspto-grants-1989_12
ORD ID	ord-f81d366078034e35837fc799910c0f83
Source note	uspto-grants-1989_12