Hydrochloric Acid → (1,3-Dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)acetic acid

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Ethyl bromoacetate	HCID 7748	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	2,2-Diethyl-6-hydroxy-4,5-dimethyl-1H-indene-1,3(2H)-dione	HCID 21516787	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(1,3-Dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)acetic acid	HCID 21516773	—

Reaction Conditions

Temperature	65 °C

Reaction Steps

A stirred mixture of 2,2-diethyl-4,5-dimethyl-6-hydroxy-indan-1,3-dione (3.5 g., 0.014 mole), ethyl bromoacetate (2.7 g., 0.016 mole) and potassium carbonate (2.2 g., 0.016 mole) in dimethylformamide (20 ml.) is heated at 65°C. for two hours, treated with methanol (40 ml.) and potassium hydroxide (1.1 g., 0.02 mole) refluxed for 1/2 hour then poured into dilute hydrochloric acid (500 ml.) affording 4.2 g. of (1,3-dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy-acetic acid which melts at 134° 136°C. after recrystallization from acetic acid-water.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US03976681
Source dataset	uspto-grants-1976_08
ORD ID	ord-f3920d4566634d2fa687c10084229d49
Source note	uspto-grants-1976_08