Acetic Acid → 4-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Tetrabutylammonium Fluoride	HCID 2724141	—
Reactant	4-(4-Chlorophenyl)-1-(4-t-butyldiphenylsiloxy phenyl)butanol	HCID 53857806	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol	HCID 19745872	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

At 0° C., 1M tetrabutylammonium fluoride (100 mL) was added to a solution of the silyl ether of Step 2 (34 g) and AcOH (15 mL) in THF (200 mL) and the reaction mixture was stirred at 0° C. 2.5 hours. 25% aqueous NH4OAc was then added and the product was extracted with EtOAc, dried over MgSO4 and purified by a swish in EtOAc:hexane 1:2. The title compound so obtained was used as such for the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05232916
Source dataset	uspto-grants-1993_08
ORD ID	ord-fd7a1b5326a241b2b75c562504967ad6
Source note	uspto-grants-1993_08