3-Hydroxybenzaldehyde → 3-Ethoxybenzaldehyde

HRID 1666837Notes

Reaction equation

HRID 1666837 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH2:11][CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cl-].[Na+].O>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH3:12]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 6340IodoethaneHCID 10796Cesium carbonate

Product 1

HCID 899083-Ethoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine 3-hydroxybenzaldehyde (5.6 g, 46 mmol) and 1-iodoethane (10.7 g, 69 mmol) in DMSO (25 mL) and warm to 80° C. Treat with of cesium carbonate (22.4 g, 69 mmol) in portions. During the addition the temperature begin to rise so the bath is removed. Stir the reaction at 80° C. for 1 hour, pour into 200 mL brine and extract twice with 150 mL diethyl ether. Wash the combine extracts twice with 200 mL brine, dry over MgSO4 and concentrate under vacuum to give an oil. Purification by chromatography (SiO2; 2.5% EtOAc in hexanes) affords 5.73 g (38 mmol; 83%) of the title compound as an oil: 1H NMR (CDCl3) 9.94 (s, 1H), 7.42-7.41 (m, 2H), 7.36-7.35 (m, 1H), 7.16-7.13 (m, 1H), 4.10-4.04 (q, 2H), 1.64-1.40 (t, 3H).

Workup

  1. additionDuring the addition the temperature
  2. customis removed
  3. customthe reaction at 80° C. for 1 hour
  4. extractionextract twice with 150 mL diethyl ether
  5. washWash the combine
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate under vacuum
  8. customto give an oil
  9. customPurification by chromatography (SiO2; 2.5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2509ea0d753040be989507268f49b3b4
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

Loading…