Ethanol → Ethyl 3-iodo-2-methylbenzoate

HRID 706125Notes

Reaction equation

HRID 706125 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-0866a633a1a140089b3352acfd5343c3
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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