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33632-34-7

5-methyl-2,3-dihydro-1,4-benzodioxine synthesis

2synthesis methods
-

Yield:33632-34-7 21.8%

Reaction Conditions:

with potassium carbonate in ethylene glycol at 130; for 48 h;Inert atmosphere;

Steps:

Intermediate: 5-methyl-2,3-dihydrobenzo[b][1,4]dioxine

Intermediate: 5-methyl-2,3-dihydrobenzo[b][1,4]dioxine
A mixture of 3-methylbenzene-1,2-diol (4 g, 32.2 mmol), 1,2-dibromoethane (24.21 g, 129 mmol), potassium carbonate (8.91 g, 64.4 mmol) in ethylene glycol (160 mL) was heated to 130° C. under N2 for 48 hrs.
The reaction mixture was cooled to rt, and poured into brine (320 mL).
The mixture was extracted with EtOAc.
The organic layer was washed with brine, dried over Mg2SO4, and the solvent was removed.
The residue was purified by silica gel column chromatography (Biotage 40m, EtOAc/Hexane=0 to 40%) to give 1.02 g (21.8%) of the target compound. 1H NMR (500 MHz, CHLOROFORM-d) δ 6.79-6.71 (m, 3H), 4.34-4.30 (m, 2H), 4.29-4.25 (m, 2H), 2.23 (s, 3H).

References:

US2017/107202,2017,A1 Location in patent:Paragraph 2039; 2040