3,4-Dihydroxybenzaldehyde → 4-Hydroxy-3-propoxybenzaldehyde

HRID 898187Notes

Reaction equation

HRID 898187 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

HCID 87683,4-DihydroxybenzaldehydeHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 17126234-Hydroxy-3-propoxybenzaldehydeYield 143.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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

  1. stirringthe reaction was stirred at 80° C. for 2.5 h
  2. washwashed with 2N HCl and water
  3. 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

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