Phenol → 1-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-ol

Participants

Reaction Conditions

Reaction Steps

A steel bomb, fitted with an internal thermocouple, pressure gauge and safety release valve rated at 3000 psi, with ˜55 mL capacity was charged with the potassium salt of 2-methoxy-4-nitrophenol (6 g, 29 mmol), NaH2PO4 (3.3 g, 27.7 mmol), isobutylene oxide (2.8 g, 35 mmol) and 30 mL of 15% H2O/MeCN. The sealed bomb was heated at 170° C. for three hr. Following cooling, HPLC revealed all starting phenol had been converted to product. The biphasic solution was concentrated using a rotary evaporator before being partitioned between CH2Cl2 and H2O. The aqueous phase was extracted 3× with CH2Cl2; the combined CH2Cl2 fractions were washed 3× with aq KHCO3/K2CO3 and once with H2O. After drying over Na2SO4, concentration under vacuum yielded 6.9 g of desired product as a tan solid.

Provenance & Evidence