Water → 3-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Methanesulfonic acid 4-tert-butyl-cyclohexyl ester	HCID 11128255	—
Reactant	4-Methylnaphthalen-2-ol	HCID 12580928	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	tert-Butanol	HCID 6386	—
Solvent	Methyl Ethyl Ketone	HCID 6569	—
Product	3-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene	HCID 68172797	48.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 4-methyl-naphthalen-2-ol (0.60 g, 3.8 mmol), methanesulfonic acid 4-tert-butyl-cyclohexyl ester (1.9 g, 7.6 mmol) and cesium carbonate (3.7 g, 11 mmol) in t-BuOH (10 mL) and 2-butanone (7 mL) was heated at 80° C. overnight. After cooled to room temperature, the mixture was treated with water and ether. The organic phase was dried over MgSO4, filtered and concentrated. The crude was treated with methanol to give solid product (0.55 g, yield: 48%). ESI-MS: 297.20 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09186367B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-a9626654858a4b39b17619976850dcd3
Source note	uspto-grants-2015_11