Hydrochloric Acid → Ethyl 2-chloro-6-formyl-4-propylbenzoate

HRID 2100589Notes

Reaction equation

HRID 2100589 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH3:15])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH:7]2[OH:12].C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH3:15])[CH:5]=[C:6]([CH:7]=[O:12])[C:10]=1[C:9]([O:8][CH2:23][CH3:24])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69052024(+/-)-7-Chloro-3-hydroxy-5-propylisobenzofuran-1(3H)-one

Product 1

HCID 86090107Ethyl 2-chloro-6-formyl-4-propylbenzoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-7-chloro-3-hydroxy-5-propylisobenzofuran-1 (3H)-one (0.66 g, 2.91 mmol) in 10 mL of DMF was added potassium carbonate (0.80 g, 5.82 mmol) followed by iodoethane (0.26 mL, 3.20 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was cooled to 0° C. and carefully acidified with 6N HCl, diluted with water and extracted with EtOAc. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.69 g (93%) of the title compound which was used without purification. 1H NMR (CDCl3): δ 9.88 (s, 1H), 7.52 (d, 1H, J=1.4 Hz), 7.40 (d, 1H, J=1.6 Hz), 4.42 (q, 2H, J=7.1 Hz), 2.60 (t, 2H, J=7.7 Hz), 1.64-1.55 (m, 2H), 1.34 (t, 3H, J=7.1 Hz), 0.89 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionextracted with EtOAc
  3. washThe organics were washed with sat'd aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b3a8e07ef4d4a5d865e0831c9c15048
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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