Water → Rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1,1-Dichloroethane	HCID 6365	—
Reactant	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone	HCID 6775	—
Reactant	Rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde	HCID 87604503	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde	HCID 87604907	64.9%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To 44 mg (0.07 mmol) of rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde in 2 mL of dichloroethane 33 mg (0.15 mmol) of DDQ and a drop of water were added. The reaction mixture was stirred at 70° C. overnight, cooled to room temperature and was diluted with dichloromethane and EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography on silica gel with EtOAc/n-heptane 1:5 gave 22 mg (62%) of rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde, MS: 483 (M−H)−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07473705B2
Source dataset	uspto-grants-2009_01
ORD ID	ord-ee6562bdd8364dfe9d7b715e977ab8a4
Source note	uspto-grants-2009_01