4-(2,2-diethoxyethoxy)toluene synthesis
- Product Name:4-(2,2-diethoxyethoxy)toluene
- CAS Number:66614-56-0
- Molecular formula:C13H20O3
- Molecular Weight:224.3
Yield:66614-56-0 100%
Reaction Conditions:
Stage #1: p-cresolwith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 0.5 h;
Stage #2: Bromoacetaldehyde diethyl acetal in N,N-dimethyl-formamide;mineral oil;Reflux;
Steps:
15.1 1-(2,2-Diethoxyethoxy)-4-methylbenzene
4-Methylphenol (3.0 g, 27.74 mmol) was dissolved in 100 dimethylformamide (30 mL), and it was cooled to 0° C. 101 NaH (60% dispersed in oil, 1.22 g, 30.50 mmol) was added in portions. The reaction mixture was then stirred for 30 min at room temperature. Then, 102 2-bromo-1,1-diethoxyethane was added. The reaction mixture was then refluxed overnight. The reaction mixture was cooled, and it was diluted with ethyl acetate. The organic layer was washed with water followed by brine. The organic layer was dried over Na2SO4 and was concentrated under reduced pressure to give the 103 product as brown oil (5.69 g, 100%); 1H NMR (300 MHz) (CDCl3) δ 7.07 (d, J=9 Hz, 2H), 6.82 (dd, J=6 Hz, J=2 Hz, 2H), 4.83 (t, J=5 Hz, 1H), 3.98 (d, J=5 Hz, 2H), 3.81-3.58 (m, 4H), 2.28 (s, 3H), 1.25 (t, J=7 Hz, 6H).
References:
US2019/31624,2019,A1 Location in patent:Paragraph 0446-0447
