Water → HCID 20510022, compound

HRID 1758275Notes

Reaction equation

HRID 1758275 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11].N1C=CC=CC=1.O.[Cl:23][CH2:24]Cl>>[Cl:23][CH2:24][C:14]1[CH:13]=[CH:12][C:9]2[C:10]([CH3:11])=[C:6]([CH3:5])[O:7][C:8]=2[CH:15]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 2734646Benzofuran, 2,3-dimethyl-

Product 1

HCID 20510022HCID 20510022, compoundYield 76.4%

Procedure

Thionyl chloride (13.1 g, 0.11 mol) was added slowly to a stirred solution of 2,3-dimethylbenzofuran (18.0 g, 0.10 mol) and pyridine (8.3 cm3, 0.105 mol) in dichloromethane (170 cm3) at below 5° C., and the solution was heated under reflux for 3 hr. The solution was poured into water and separated, the organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed to give 6-chloromethyl-2,3-dimethylbenzofuran (16.2 g, 0.078 mol, 76.4%). (Found: C, 67.76; H, 5.65; Cl, 18.21. C11H11ClO requires C, 67.87; H, 5.70; Cl, 18.22%) m.p. 63°-65° C. [ex petroleum ether (b.p. 60°-80° C.)].

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hr
  3. customseparated
  4. washthe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-7887b5bb3a5142728c0ffacbce8f8ad3
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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