Dimethylformamide → 2,6-Dimethoxy-4-hydroxybenzaldehyde

To a solution of 3,5-dimethoxyphenol (50 g, 320 mmol) in phosphorous oxychloride (60 mL, 650 mmol) at 0° C. was added dimethylformamide (37 mL, 490 mmol) over a period of 30 min and the mixture was warmed to room temperature and stirred overnight. The mixture was added to icewater (600 mL) and the mixture was washed with ether (3×200 mL). Then an 32% aqueous solution of sodium hydroxide was added until pH was 5.5 and the compound precipitated. The precipitate was separated and washed with water (100 mL) and ether (100 mL) and dried in vacuo. The precipitate was recrystallized from ethanol (600 mL) to give 22.6 g of 4-formyl-3,5-dimethoxyphenol.

1. additionThe mixture was added to icewater (600 mL)
2. washthe mixture was washed with ether (3×200 mL)
3. additionThen an 32% aqueous solution of sodium hydroxide was added until pH was 5.5
4. customthe compound precipitated
5. customThe precipitate was separated
6. washwashed with water (100 mL) and ether (100 mL)
7. customdried in vacuo
8. customThe precipitate was recrystallized from ethanol (600 mL)

ORD record

ord-1f0cb223f5224888a0cd0722308c3091

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127391