Sodium Methoxide → 4-Methoxycarbonylmethyl-3-nitrophenol

Temperature

20 °C

To a stirred suspension of 4-methoxycarbonylmethyl-3-nitrophenyl benzoate (26.2 g, 79 mmol) in methanol (600 mL) at 20° C. was added, dropwise over 0.3 h, a solution of sodium methoxide (4.7 g, 87 mmol) in methanol (300 mL). The resulting mixture was stirred at 20° C. for 2 h then at 50° C. for 1 h. The solution was concentrated to 200 mL in vacuo, then poured into water (1 L) and extracted with ether-hexane (1:5, 500 mL). The aqueous phase was neutralised with 2 M hydrochloric acid, then extracted with dichloromethane (6×300 mL). The combined dichloromethane extracts were dried (Na2SO4) and evaporated in vacuo to give a semi-solid, which was triturated with ether-hexane (1:3, 2×100 mL) to give the title compound (15.3 g, 85%) as a yellow solid.

1. additionwas added, dropwise over 0.3 h
2. waitat 50° C. for 1 h
3. concentrationThe solution was concentrated to 200 mL in vacuo
4. additionpoured into water (1 L)
5. extractionextracted with ether-hexane (1:5, 500 mL)
6. extractionextracted with dichloromethane (6×300 mL)
7. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
8. customevaporated in vacuo
9. customto give a semi-solid, which
10. customwas triturated with ether-hexane (1:3, 2×100 mL)

ORD record

ord-1631c796674b4156b58c9520f80c99bb

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06939871B2