2,4-Dihydroxybenzaldehyde → Benzaldehyde, 2-hydroxy-4-(octyloxy)-

HRID 1872359Notes

Reaction equation

HRID 1872359 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(#N)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 10060673Benzaldehyde, 2-hydroxy-4-(octyloxy)-Yield 67.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,4-Dihydroxybenzaldehyde (5.52 g), potassium carbonate (6.08 g) and octyl bromide (7.73 g) in acetonitrile (55 ml) was stirred for 16 hours at 60° C. The solvent of reaction mixture was removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with water and brine. The separated organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane : ethyl acetate=9:1) to give 2-Hydroxy-4-octyloxybenzaldehyde (6.73 g).

Workup

  1. customThe solvent of reaction mixture
  2. customwas removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe separated organic layer was dried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. washeluted with (hexane : ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a0acda62e0e748f2921e5151bcc56ce5
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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