alpha-Chloro-o-xylene → HCID 12939246, compound

HRID 1833846Notes

Reaction equation

HRID 1833846 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([O:17][CH3:18])=[O:16]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:14]1[O:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11093alpha-Chloro-o-xyleneHCID 11902Methyl 2-furoate

Product 1

HCID 12939246HCID 12939246, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-methylbenzyl chloride [prepared as described by Voronkov and Popova, Latv. P.S.R. Zinat. Akad. Vestis Kim. Sev. 1970(5), 595; 62 g.], methyl 2-furoate (114 g.) and anhydrous ferric chloride (1.4 g.) in dry carbon tetrachloride (120 ml.) was heated on a steam bath under relfux for 18 hours. The solution was then evapoated to dryness. The residue was dissolved in chloroform, washed with 2N hydrochloric acid and water, dried over magnesium sulphate and distilled to give methyl 5-(2-methylbenzyl)-2-furoate (50 g.) in the form of a yellow coloured oil, b.p. 140°-170° C./0.1-0.5 mm.Hg.

Workup

  1. temperaturewas heated on a steam bath under relfux for 18 hours
  2. washwashed with 2N hydrochloric acid and water
  3. dry with materialdried over magnesium sulphate
  4. distillationdistilled

Sources & evidence

ORD record
ord-3f0457abdbf540a4b8843214433509cf
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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