Ethanol → Ethyl 3-iodo-2-methylbenzoate

HRID 2077118Notes

Reaction equation

HRID 2077118 reaction equation
[I:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[CH2:16]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[C:3]=1[CH3:11])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 27348883-Iodo-2-methylbenzoic acid

Product 1

HCID 54051219Ethyl 3-iodo-2-methylbenzoate

Procedure

To a stirred solution of 3-iodo-2-methyl-benzoic acid (30 g, 0.11 mol) in ethanol (425 mL) was added thionyl chloride (42 mL, 0.57 mol) at 0° C. The mixture was refluxed for 4.5 h before it was cooled to room temperature and concentrated in vacuo. The residue was partitioned between ethyl ether and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over anhydrous sodium sulfate and was concentrated in vacuo to give the title compound as a pale yellow oil (32.28 g): 1H NMR (CDCl3, 200 MHz): δ=7.94 (d, J=7.8 Hz, 1H), 7.70 (d, J=7.4 Hz, 1H), 6.90 (t, J=7.8 Hz, 1H), 4.35 (q, J=7.2 Hz, 2H), 2.65 (s, 3H), 1.38 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe mixture was refluxed for 4.5 h before it
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl ether and saturated sodium bicarbonate solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-3ba00f323278471cb6af5e5572c15898
Source dataset
uspto-grants-2011_04
Patent number
US07928120B2

Reaction notes

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