4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

HRID 859863Notes

Reaction equation

HRID 859863 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 141069p-DodecyloxybenzaldehydeYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

4-Hydroxybenzaldehyde (673 mg, 5.5 mmol), 1-bromododecane (1.25 g, 5 mmol) and potassium carbonate (859 mg, 6.22 mmol) were added to dimethylformamide (3 ml), and they were stirred at 65° C. for 18 hours. After the completion of the reaction followed by the extraction with ethyl acetate, 4-dodecyloxybenzaldehyde (yield: 1.45 g, 99%) was obtained in the form of white crystals.

Workup

  1. extractionAfter the completion of the reaction followed by the extraction with ethyl acetate

Sources & evidence

ORD record
ord-12fa859137724c1189024c562e816932
Source dataset
uspto-grants-2006_12
Patent number
US07153850B2

Reaction notes

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