Ammonia → 5-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	p-Toluenesulfonic acid	HCID 6101	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2',3'-Dihydrospiro[[1,3]dioxolane-2,1'-inden]-5'-yl)methanol	HCID 69201996	—
Solvent	Acetone	HCID 180	—
Solvent	Water	HCID 962	—
Product	5-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one	HCID 69198532	—

Reaction Steps

A solution of Example 332B (8.0 g, 38.7 mmol) and p-toluenesulfonic acid (7.4 g, 38.7 mmol) in a mixture of water (20 mL) and acetone (85 mL) was refluxed for about 1 hour. The mixture was concentrated in vacuum, diluted with water and was neutralized by careful addition of potassium carbonate (2.7 g, 19.4 mmol). The precipitate was filtered off, washed with a minimum of water and diethyl ether and was dried in vacuum to give the above intermediate. MS (DCI/NH3): m/z 180 (M+NH4)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07320986B2
Source dataset	uspto-grants-2008_01
ORD ID	ord-da7fb63b8aac4709ba02e30cc2267dac
Source note	uspto-grants-2008_01