Water → 2-Methoxy-4-(2-tetrahydrofuranylmethoxy)benzaldehyde

HRID 1056810Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18](Br)[CH:19]1[O:23][CH2:22][CH2:21][CH2:20]1.O>CN1CCCC1=O>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([O:1][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][O:23]2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

In 160 mL of N-methylpyrrolidone was dissolved 24.5 g (161 mmol) of 4-hydroxy-2-methoxybenzaldehyde. To this solution were added 63 g (0.19 mol) of cesium carbonate and 40 g (0.24 mol) of tetrahydrofurfuryl bromide at room temperature and the mixture was stirred at 80° C. for 22 hours. Water (800 mL) was added to the resulting reaction mixture under ice-cooling, and extraction with diethyl ether (500 mL×3 times) was performed. The combined organic layer was washed with water and then with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting crude product was purified on basic alumina (hexane/ethyl acetate=50/50 to 0/100) to give 23.7 g (62% yield) of the title compound as a light yellow powder with the following properties.

Workup

temperaturecooling
extractionextraction with diethyl ether (500 mL×3 times)
washThe combined organic layer was washed with water
dry with materialwith saturated brine and dried over anhydrous sodium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customThe resulting crude product was purified on basic alumina (hexane/ethyl acetate=50/50 to 0/100)

Sources & evidence

ORD record: ord-db6f42afe1b04366b2ee42dfd64840c0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399635B2

Reaction notes

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