3-Hydroxybenzaldehyde → 3-[[5-(Acetyloxy)pentyl]oxy]benzaldehyde

HRID 1648009

Reaction equation

HRID 1648009 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOCC>[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 851405-Bromopentyl acetate

Product 1

HCID 199221103-[[5-(Acetyloxy)pentyl]oxy]benzaldehydeYield 103.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.22 g (10 mmol) of 3-hydroxybenzaldehyde, 2.3 g (11 mmol) of 5-bromopentyl acetate, 3.82 g (27.7 mmol) of anhydrous, granular potassium carbonate, and 25 mL of dimethyl sulfoxide was stirred at room temperature for 20 hr. The resulting brown slurry was diluted with ether and washed with water and saturated brine. Completion of the usual work-up gave 2.59 g (100%) of 3-[[5-(acetyloxy)pentyl]oxy]benzaldehyde as a yellow oil which was used without further purification.

Workup

  1. washwashed with water and saturated brine

Sources & evidence

ORD record
ord-15a3040a6586440e87e7b4658ec843c7
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Linked notes

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