3-Hydroxybenzaldehyde → 3-Propoxybenzaldehyde

HRID 1666865Notes

Reaction equation

HRID 1666865 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](I)[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:10]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 27604693-Propoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Combine 3-hydroxybenzaldehyde (7.50 gm; 61.4 mmol), n-propyl iodide (17.3 gm; 102 mmol), and potassium carbonate (16.90 gm; 122 mmol) in 2-butanone (100 mL) and reflux. After 17 h, allow the mixture to cool to room temperature, decant the solution and concentrate by rotary evaporation. Partition the residue between diethyl ether (150 mL) and water (150 mL), separate the layers and extract the aqueous layer with diethyl ether (2×100 mL). Combine organic layers and wash with water, 1 N NaOH, and then water, dry over MgSO4, and concentrate to give a residue. Distill the residue to give the title compound: bp: 122-125° C. (15 mm); TLC (10% Et2O/hexanes; Rf 0.35).

Workup

  1. customdecant the solution
  2. concentrationconcentrate by rotary evaporation
  3. customPartition the residue between diethyl ether (150 mL) and water (150 mL)
  4. customseparate the layers
  5. extractionextract the aqueous layer with diethyl ether (2×100 mL)
  6. washCombine organic layers and wash with water, 1 N NaOH
  7. dry with materialwater, dry over MgSO4
  8. concentrationconcentrate
  9. customto give a residue
  10. distillationDistill the residue

Sources & evidence

ORD record
ord-1968699b6a8345658918b29877af5067
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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