Methanol → Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-hydroxybenzoate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)	HCID 466102	—
Reactant	Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate	HCID 57467622	—
Product	Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-hydroxybenzoate	HCID 57467624	81.6%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a stirred solution of 66.18C (2.500 g, 7.85 mmol) in MeOH (10.00 mL, 7.85 mmol) at 23° C. was added PPTS (0.197 g, 0.785 mmol). The reaction was heated to 60° C. and stirred for 19 hours. The reaction was then concentrated in vacuo to give a clear oil. The product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.18D as a colorless oil (1.50 g, 81.5% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030354B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-bc5a4e3512804c8c9f2c8f06e6681d1b
Source note	uspto-grants-2011_10