1,3-Dibromopropane → HCID 53973893, compound

HRID 361708Notes

Reaction equation

HRID 361708 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[CH2:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[OH:23])[CH:18]=[O:19])[CH:13]=[CH2:14]>CC(C)=O>[CH2:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH2:4][CH2:3][CH2:2][Br:1])[CH:18]=[O:19])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 47290143-Allyl-4-hydroxybenzaldehyde

Product 1

HCID 53973893HCID 53973893, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,3-Dibromopropane (15.76 ml) and potassium carbonate (4.69 g) were added to a solution of 3-allyl-4-hydroxybenzaldehyde (5 g) in acetone and the reaction mixture heated at reflux for 16 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue purified by flash column chromatography on silica gel (Merck Art No 9385) using a 10:90 (v/v) mixture of ethyl acetate/hexane as eluent to give 3-allyl-4-(3-bromopropoxy)benzaldehyde (4.86 g) as an oil which slowly solidified. NMR([CD3 ]2SO): 2.2-2.4(2H,m), 3.35-3.50(2H,m), 3.65-3.80(2H,t), 4.2-4.3(2H,t), 5.0-5.15(2H,m), 5.8-6.1(1H,m), 7.15-7.25(1H,d), 7.7(1H,d), 7.75-7.85(1H,q) and 9,85(1H,s).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue purified by flash column chromatography on silica gel (Merck Art No 9385)
  6. additiona 10:90 (v/v) mixture of ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-84219d9be37a442fa1ce8c6e3c548024
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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