Water → 3,4,5-Trimethoxybenzyl alcohol

3,4,5-trimethoxybenzaldehyde (15 g, 76.45 mmol) and anhydrous alcohol (200 ml) were placed in a 250 ml three-necked flask, and were dissolved at 40° C. Sodium borohydride (1.48 g, 38.23 mmol) was added to the solution. The resulting mixture was heated to reflux for 45 minutes, and monitored by TLC. When the reaction is completed, cooling it to room temperature, deionized water (10 ml, 555.8 mol) was added to quench the reaction. After suction filtering, the filter residue was washed by anhydrous alcohol (20 ml), the combined filtrate was concentrated in rotatory evaporater to dry, dichlormethane (100 ml) was added to dissolve the crude product. The organic layer was washed with sodium hydroxide solution (50 ml) twice and with deionized water (50 ml) twice, and a proper amount of anhydrous magnesium sulfate was added to dry it overnight. After filtering, washing the filter residue with dichlormethane (20 ml). The combined filtrate was concentrated in a rotatory evaporator to afford 3,4,5-trimethoxyl benzyl alcohol, 14.05 g of colorless oily product, yield: 92.72%

1. dissolutionwere dissolved at 40° C
2. temperatureThe resulting mixture was heated
3. temperatureto reflux for 45 minutes
4. customto quench
5. customthe reaction
6. filtrationAfter suction filtering
7. washthe filter residue was washed by anhydrous alcohol (20 ml)
8. concentrationthe combined filtrate was concentrated in rotatory evaporater
9. customto dry
10. additiondichlormethane (100 ml) was added
11. dissolutionto dissolve the crude product
12. washThe organic layer was washed with sodium hydroxide solution (50 ml) twice
13. additionwith deionized water (50 ml) twice, and a proper amount of anhydrous magnesium sulfate was added
14. customto dry it overnight
15. filtrationAfter filtering
16. washwashing the filter residue with dichlormethane (20 ml)
17. concentrationThe combined filtrate was concentrated in a rotatory evaporator

ORD record

ord-f990063dd0024e9d8e509a4bdc378276

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632863B2