2,4-Dihydroxybenzaldehyde → 4-(Hexyloxy)-2-hydroxybenzaldehyde

HRID 859866Notes

Reaction equation

HRID 859866 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 81011-BromohexaneHCID 11125Lithium Carbonate

Product 1

HCID 131472364-(Hexyloxy)-2-hydroxybenzaldehydeYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dihydroxybenzaldehyde (3.00 g, 21.7 mmol) and hexyl bromide (7.62 ml, 54.3 mmol) were stirred in the presence of lithium carbonate (4.00 g, 54.3 mmol) in dimethylformamide (5 ml) at 55° C. overnight. After the neutralization with hydrochloric acid followed by the extraction with ethyl acetate, the product was purified by the silica gel column chromatography to obtain 4-hexyloxy-2-hydroxybenzaldehyde (yield: 1.77 g, 37%) in the form of a colorless oil.

Workup

  1. extractionAfter the neutralization with hydrochloric acid followed by the extraction with ethyl acetate
  2. customthe product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-8f761f7b889644f7baae44f59c472333
Source dataset
uspto-grants-2006_12
Patent number
US07153850B2

Reaction notes

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