Water → 2-Methoxymethyloxy-3,4,5,6-tetramethoxybenzaldehyde

HRID 1770241Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[O:17][CH3:18].C([Li])CCC.CN([CH:27]=[O:28])C.O>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[C:10]=1[CH:27]=[O:28]

Participants

Conditions

Temperature: -20 °C

Procedure

6.2 g of 1-methoxymethyloxy-2,3,4,5-tetramethoxybenzene prepared in Referential Example 13 was dissolved in 50 ml of anhydrous ether, and 18 ml of n-butyllithium (1.6M n-hexane solution) was dropwise added thereto at -20° C. while stirring. After the mixture was stirred at 0° C. for 30 min, the temperature was returned to -20° C. and 3.5 ml of DMF was dropwise added thereto. After 100 ml of water was added thereto, the mixture was extracted with ethyl acetate, and the organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3) to prepare 5.6 g of the product compound as a light yellow oleaginous substance.

Workup

stirringAfter the mixture was stirred at 0° C. for 30 min
customwas returned to -20° C.
extractionthe mixture was extracted with ethyl acetate
washthe organic phase was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3)
customto prepare 5.6 g of the product compound as a light yellow oleaginous substance

Sources & evidence

ORD record: ord-73a55a75cb0f4a6b8754766dafcfa860
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05385942

Reaction notes

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