1,2,4-Trimethylbenzene → HCID 76774163, compound

HRID 2408253Notes

Reaction equation

HRID 2408253 reaction equation
C([O:5][CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C(C)=C)C=CC.[C:16]1([C:18](=[CH:20][C:21](=[CH:23][CH:24]=1)C)C)[CH3:17]>>[CH2:15]([CH:10]([CH2:11][C:12]([CH3:13])=[CH:17][C:16]1[CH:24]=[CH:23][CH:21]=[CH:20][CH:18]=1)[CH:6]=[O:5])[CH3:14]

Participants

3

Reactant 2

HCID 72471,2,4-TrimethylbenzeneHCID 67331219HCID 67331219, compound

Product 1

HCID 76774163HCID 76774163, compoundYield 51%

Procedure

The [1-(2-butenyloxy)-2-methyl-2-propenyl]benzene (26.9 g, 0.126 mol), [RuCl2(PPh3)3] (280 mg), BHT (100 mg) and pseudo-cumene (25 ml) were heated together in an autoclave placed in an oil bath at 180° C. for 4 hours. After cooling to room temperature, the pseudo-cumene was distilled off (40° C./5 mbar) and the residue purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 50:1 to 10:1) followed by bulb-to-bulb distillation (87° C./0.008 mbar). 13.0 g of the desired product were obtained (yield=51%) as a 9:1 mixture of E/Z isomers.

Workup

  1. distillationthe pseudo-cumene was distilled off (40° C./5 mbar)
  2. customthe residue purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 50:1 to 10:1)
  3. distillationfollowed by bulb-to-bulb distillation (87° C./0.008 mbar)

Sources & evidence

ORD record
ord-1efadf9484f8409f8a808fbffe5f6fcb
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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