3-Hydroxybenzaldehyde → 3-Ethoxybenzaldehyde

HRID 1666889Notes

Reaction equation

HRID 1666889 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 5.6 g of 3-hydroxybenzaldehyde (46 mmol) and 10.7 g of 1-iodoethane (69 mmol) in DMSO (25 mL) and warm to 8° C. and treat with 22.4 g of cesium carbonate (69 mmol) portionwise and stir. After 1 hour, pour into 200 mL brine and extract twice with 150 mL diethyl ether. Combine the extracts and wash 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 desired 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. extractionextract twice with 150 mL diethyl ether
  2. washwash twice with 200 mL brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate under vacuum
  5. customto give an oil
  6. customPurification by chromatography (SiO2; 2.5% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-26030ba6a6ae496f9d1ebb4b2727cfbd
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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