2-Hydroxy-5-methoxybenzaldehyde → 2-(hydroxymethyl)-4-methoxyphenol

To a suspension of sodium borohydride (2.50 g, 65.8 mmol) in ethanol (100 mL) at 5° C. was added a solution of 2-hydroxy-5-methoxybenzaldehyde (10.00 g, 65.8 mmol) in ethanol (35 mL) dropwise. Upon completion of the addition the reaction mixture was allowed to stir for ten minutes then quenched by the dropwise addition of 10% aqueous acetic acid (75 mL). The ethanol was removed by concentration in vacuo and the resulting mixture poured into water (250 mL) and extracted with ethylacetate (3×100 mL). The combined extracts were washed sequentially with saturated sodium bicarbonate (50 mL), and brine (3×100 mL). The organic extract was dried (Na2SO4) and concentrated to afford a crude product (8.75 g). Trituration with hexane:ether (3:2, 25 mL) afforded 2-hydroxy-5-methoxybenzyl alcohol (7.00 g, 70%) as a white solid.

1. additionUpon completion of the addition the reaction mixture
2. customthen quenched by the dropwise addition of 10% aqueous acetic acid (75 mL)
3. customThe ethanol was removed by concentration in vacuo
4. additionthe resulting mixture poured into water (250 mL)
5. extractionextracted with ethylacetate (3×100 mL)
6. washThe combined extracts were washed sequentially with saturated sodium bicarbonate (50 mL), and brine (3×100 mL)
7. extractionThe organic extract
8. dry with materialwas dried (Na2SO4)
9. concentrationconcentrated
10. customto afford a crude product (8.75 g)

ORD record

ord-ac36c031a5964613aba1d74687b7b2f4

Source dataset

uspto-grants-1986_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04596828