3-Methoxybenzaldehyde → 28446-69-7

Diethylcyanomethyl phosphonate (28.6 mL, 176 mmol) was added to a suspension of NaH (7.0 g, 176 mmol, washed with hexanes to remove oil) in 450 mL of THF at RT and the resulting mixture was stirred at RT for 30 min. A solution of m-anisaldehyde (20.0 g, 140 mmol) in 50 mL of THF was added and the resulting mixture was stirred at RT overnight, resulting in the formation of a thick brown oil at the bottom of the mixture. The crude reaction mixture was concentrated in vacuo and the residue was partitioned between saturated aqueous NaHCO3 solution and methylene chloride. The organic phase was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were then dried over MgSO4, filtered, and concentrated in vacuo to provide 27.6 g of a brown oil (99% crude yield) which was carried on without further purification. 1H NMR (CDCl3) δ 7.30-7.40 (m, 2H), 6.92-7.05 (m, 3H), 5.86 (d, J=24 Hz, 1H), 3.85 (s, 3H).

1. stirringthe resulting mixture was stirred at RT overnight
2. customresulting in the formation of a thick brown oil at the bottom of the mixture
3. customThe crude reaction mixture
4. concentrationwas concentrated in vacuo
5. customthe residue was partitioned between saturated aqueous NaHCO3 solution and methylene chloride
6. customThe organic phase was separated
7. extractionthe aqueous phase was extracted with methylene chloride
8. dry with materialThe combined organic phases were then dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-fa2d003413f24513b2bb100485fbd33a

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05661185