Iodoethane → Ethyl 2-formylbenzoate

HRID 1612653Notes

Reaction equation

HRID 1612653 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].C(=O)(O)[O-].[Na+].I[CH2:18][CH3:19]>CN(C)C=O.O>[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[C:1]([O:3][CH2:18][CH3:19])=[O:2])=[O:7]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8406Phthalaldehydic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10943020Ethyl 2-formylbenzoateYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Carboxybenzaldehyde (2.018g, 13.4 mmol, 1.0 eq.) was combined with sodium bicarbonate (2.258 g, 26.9 mmol, 2.0 eq.) and iodoethane (2.15 ml, 26.9 mmol, 2.0 eq.) in dimethylformamide (13.4 ml, 1M) and stirred at room temperature for 16 hours. The reaction was diluted with water (25 ml) and extracted with ether: hexane (1:1, 3X20 ml). The combined organic extracts were washed with aqueous 10% sodium bisulfite (1X25 ml), water (1X25 ml) and aqueous saturated sodium chloride (1X25 ml), dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on Merck silica gel (20 g) eluting with hexane: ether (14:1) to provide the title A compound (1.485 g).

Workup

  1. extractionextracted with ether: hexane (1:1, 3X20 ml)
  2. washThe combined organic extracts were washed with aqueous 10% sodium bisulfite (1X25 ml), water (1X25 ml) and aqueous saturated sodium chloride (1X25 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on Merck silica gel (20 g)
  7. washeluting with hexane: ether (14:1)

Sources & evidence

ORD record
ord-0a7b05c12e5c43868b56d1007185ee87
Source dataset
uspto-grants-1993_03
Patent number
US05190942

Reaction notes

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