o-Xylyl bromide → HCID 12939246, compound

HRID 1833845Notes

Reaction equation

HRID 1833845 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[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>[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

4

Reactant 2

HCID 6992o-Xylyl bromideHCID 11902Methyl 2-furoate

Product 1

HCID 12939246HCID 12939246, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methylbenzyl bromide [prepared as described by Radziszewaki and Wispek, Ber, 15, 1747 (1882); 18.5 g.], methyl 2-furoate (15.3 g.) and anhydrous ferric chloride (0.3 g.) in dry carbon tetrachloride (25 ml.) was heated on a steam bath under reflux for 18 hours and then distilled to give crude methyl 5-(2-methylbenzyl)-2-furoate (7.7 g.) in the form of a pale brown coloured oil, b.p. 120°-145° C./0.1 mm.Hg, suitable for use as a starting material in procedures hereinafter described.

Workup

  1. temperaturewas heated on a steam bath
  2. temperatureunder reflux for 18 hours
  3. distillationdistilled

Sources & evidence

ORD record
ord-eb9e297f74d84d159ce27d87ee18c102
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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