3-Hydroxybenzaldehyde → 3-(allyloxy)benzaldehyde

HRID 2307670Notes

Reaction equation

HRID 2307670 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10](Br)[CH:11]=[CH2:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C(=O)C.C(OCC)C>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH:11]=[CH2:10]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7841Allyl bromideHCID 10796Cesium carbonate

Product 1

HCID 27166123-(allyloxy)benzaldehydeYield 89.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

3-Hydroxybenzaldehyde (1.00 g, 8.19 mmol) and allyl bromide (0.780 mL, 9.01 mmol) in N,N-dimethylacetamide (35 mL) was treated with Cs2CO3 (4.01 g, 12.3 mmol) and allowed to stir at room temperature for 12 hours. The reaction mixture was diluted with diethyl ether (150 mL), washed with 1N HCl, saturated NaHCO3, brine, dried (MgSO4), filtered and the filtrate concentrated. The residue was purified by flash chromatography (silica gel, using 7% ethyl acetate/hexanes as eluent) to provide the title compound as a clear oil (1.19 g, 89%).

Workup

  1. washwashed with 1N HCl, saturated NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash chromatography (silica gel, using 7% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-5dd646a2b3a142b2bce2412fd8f27925
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

Loading…