Methane, dichloromethoxy- → 5-Chloro-2-methoxy-3-methylbenzaldehyde

Temperature

0 °C

Titanium tetrachloride (21.6 g, 0.114 mole) was added to a solution of 2-methyl-4-chloroanisole (9 g, 0.057 mole) in methylene chloride at 0° C. Then, 1,1-dichloromethyl methyl ether (7.24 g, 0.063 mole) was added dropwise over a three minute period and the reaction mixture stirred at 0° C. for 30 minutes. The reaction was quenched by carefully pouring it into water (600 ml). The organic layer was separated and the aqueous phase extracted with methylene chloride (2×100 ml). The combined organic layer and extracts was washed with brine, dried (MgSO4) and concentrated under reduced pressure to a pale yellow solid (10.1 g).

1. customThe reaction was quenched
2. additionby carefully pouring it into water (600 ml)
3. customThe organic layer was separated
4. extractionthe aqueous phase extracted with methylene chloride (2×100 ml)
5. washThe combined organic layer and extracts was washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated under reduced pressure to a pale yellow solid (10.1 g)

ORD record

ord-d70ad4294ed1496f811f32daceee59ea

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04617312