3,4-Dihydroxybenzaldehyde → 4-Hydroxy-3-propoxybenzaldehyde
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].I[CH2:14][CH2:15][CH3:16]>CN(C=O)C.C(OCC)(=O)C>[OH:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:14][CH2:15][CH3:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
3,4-Dihydroxybenzaldehyde (0.5 g, 3.62 mmol) was dissolved in DMF (10 mL) and sodium hydride (0.087 g, 3.62 mmol) was added. The reaction mixture was stirred at rt for 10 min. Iodopropane (0.35 mL, 0.62 mmol) was added and the reaction was stirred at 80° C. for 2.5 h. The reaction was diluted with ethyl acetate and washed with 2N HCl and water. Silica gel chromatography eluting with 35% ethyl acetate/hexane yielded 0.16 g of desired product: ESI-MS 181 (M+H).
Workup
- stirringthe reaction was stirred at 80° C. for 2.5 h
- washwashed with 2N HCl and water
- washSilica gel chromatography eluting with 35% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-cbab7b2cf3c546d3a9c078fecfbbfae0
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351725B2
Reaction notes
Loading…