Water → 4-(3-Chloropropoxy)-M-anisaldehyde

HRID 1900416Notes

Reaction equation

HRID 1900416 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22].O>CC(C)=O>[Cl:22][CH2:21][CH2:20][CH2:19][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 46108414-(3-Chloropropoxy)-M-anisaldehydeYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of vanillin (30.4 g, 200 mmol), K2CO3 (27.6 g) and acetone (150 ml) was stirred and refluxed for 0.5 hours. Heating was removed and 1-bromo-3-chloropropane (40.8 g, 260 mmol) in acetone was added dropwise. The reaction was stirred and refluxed for 16 hours, and then it was poured into water. The aqueous mixture was extracted with diethyl ether, the extract was dried (MgSO4), and the solution was concentrated to afford an oil, which upon evacuation solidified to a white solid (50.2 g). An 8.0 g sample was flash chromatographed on silica gel with 50% ethyl acetatehexane as eluent. Concentration of appropriate fractions gave 2.7 g (37%) of 4-(3-chloropropoxy)-3-methoxybenzaldehyde as a white solid, m.p.=53°-55° C.

Workup

  1. temperaturerefluxed for 0.5 hours
  2. temperatureHeating
  3. customwas removed
  4. stirringThe reaction was stirred
  5. temperaturerefluxed for 16 hours
  6. extractionThe aqueous mixture was extracted with diethyl ether
  7. dry with materialthe extract was dried (MgSO4)
  8. concentrationthe solution was concentrated
  9. customto afford an oil, which upon evacuation
  10. customchromatographed on silica gel with 50% ethyl acetatehexane as eluent

Sources & evidence

ORD record
ord-94747cd9220c4d9e8b96153d0732c422
Source dataset
uspto-grants-1996_11
Patent number
US05574032

Reaction notes

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