Water → Ethyl 2-(3,5-dimethylphenoxy)acetate

Referring to FIG. 37, to a solution of 3,5-dimethylphenol (10 g, 82 mmol) in CH3CN (150 mL) were added ethyl 2-bromoacetate (14.9 g, 90 mmol) and K2CO3 (16.9 g, 123 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was poured into water (200 mL) and the resulting mixture was extracted with ethyl acetate (150 mL×2). The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give product as a yellow oil, which was used in the next step without further purification (19 g); 1H NMR (CDCl3, 300 MHz): δ 6.13 (s, 1H), 6.11 (s, 2H), 4.59 (s, 2H), 4.30 (q, J=7.2 Hz, 2H), 3.77 (s, 6H), 1.31 (1, J=7.2 Hz, 3H).

1. extractionthe resulting mixture was extracted with ethyl acetate (150 mL×2)
2. washThe combined extracts were washed with brine
3. dry with materialdried over anhydrous Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto give product as a yellow oil, which
6. customwas used in the next step without further purification (19 g)

ORD record

ord-34843b10830740d199ca2ffc95132617

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315542B2