Hydrochloric Acid → Cyclohexanone, 4-[(phenylmethoxy)methyl]-

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Water	HCID 962	—
Reactant	8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane	HCID 10378031	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	Cyclohexanone, 4-[(phenylmethoxy)methyl]-	HCID 10443381	—

Reaction Conditions

Temperature	85 °C

Reaction Steps

To a solution of EXAMPLE 531C (43.02 g) in dioxane (500 mL) was added water (125 mL) and 2M hydrochloric acid (90 mL). The mixture was heated at 85° C. for 18 hours. Upon cooling, the reaction mixture was diluted with brine (1500 mL), saturated sodium bicarbonate solution (300 mL) and ether (1000 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified on silica gel eluting with a 5, 15, 25, 50% ethyl acetate in hexanes step gradient to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045420B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-72b475eeb5cc499091878ead501378c5
Source note	uspto-grants-2015_06