Water → 2-(Methoxymethoxy)-4-(phenylmethoxy)benzaldehyde

To a solution of 4-benzyloxy-2-hydoxy-benzaldehyde (44.9 g, 197 mmol) synthesized in step (a) of Example 197 in dichloromethane (200 ml) were added diisopropylethylamine (52.0 ml, 300 mmol) and methoxymethyl chloride (20.5 ml, 270 mmol) at 0° C. with stirring, and the resulting mixture was stirred overnight at room temperature under a nitrogen atmosphere. After stirring, water (200 ml) was added, and the resulting mixture was extracted with dichloromethane (200 ml×2). The organic layer was washed successively with water (300 ml×1) and saturated aqueous sodium chloride solution (300 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1-1:1) as the eluent to afford the title compound (42.2 g, yield: 79%) as a colorless oil.

1. stirringthe resulting mixture was stirred overnight at room temperature under a nitrogen atmosphere
2. stirringAfter stirring
3. extractionthe resulting mixture was extracted with dichloromethane (200 ml×2)
4. washThe organic layer was washed successively with water (300 ml×1) and saturated aqueous sodium chloride solution (300 ml×1)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford the crude product
9. customThe crude product was purified by chromatography on a silica gel column

ORD record

ord-d3195df1145e4c54ad6434a42ec5055a

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514475B2