1,2,3-Trichlorobenzene → 2,3-Dichloroanisole

Trichlorobenzene (363 g, 2 moles) was dissolved in 600 ml of dimethyl acetamide and 650 ml of 25% sodium methoxide in methanol solution added all at once. The solution was stirred and heated to 166° as the methanol slowly distilled out. The solution was held at 166° for 30 minutes, * cooled and quenched with 5 times its volume of water and extracted with toluene (2 × 1000 ml). The toluene extracts were washed with water (1 L) and dried over sodium sulfate. The toluene was removed by distillation under reduced pressure and the residue fractionated to yield the pure 2,3-dichloroanisole, bp 140°/28 mm. Yield 212 g (60%). Considerable material remains in the aqueous DMAC layer and can be recovered by repeated extractions with methylene chloride.

1. distillationslowly distilled out
2. temperature* cooled
3. customquenched with 5 times its volume of water
4. extractionextracted with toluene (2 × 1000 ml)
5. washThe toluene extracts were washed with water (1 L)
6. dry with materialdried over sodium sulfate
7. customThe toluene was removed by distillation under reduced pressure

ORD record

ord-eac7ee65f9bf4816bae838e7b8d6f633

Source dataset

uspto-grants-1977_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04057585