Benzene → HCID 86657622, compound

HRID 2387591Notes

Reaction equation

HRID 2387591 reaction equation
C([O:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)C=C.[CH:16]1[CH:21]=CC=C[CH:17]=1>>[CH3:15][CH:6]([CH:7]([C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:16]([CH3:21])=[CH2:17])[CH:5]=[O:4]

Participants

3

Reactant 2

HCID 241BenzeneHCID 67151185HCID 67151185, compound

Product 1

HCID 86657622HCID 86657622, compoundYield 29%

Procedure

The 1-[(1E)-3-(Allyloxy)-2-methyl-1-propenyl]-4-methylbenzene (72.7 g, 0.359 mol), [RuCl2(PPh3)3] (1.1 g), BHT (50 mg) and benzene (250 ml) were heated together in an autoclave placed in an oil bath at 165-170° C. for 24 hours. After cooling to room temperature, the benzene was evaporated under vacuum and the residue chromatographed on silica gel (eluent: heptanes/ethyl acetate 25:1 to 4:1), then distilled under vacuum through a 20-cm Widmer column. 21.3 g of the desired product were obtained (yield=29%) as a 40:60 mixture of diastereoisomers. B.P.=95° C./0.001 mbar

Workup

  1. customthe benzene was evaporated under vacuum
  2. customthe residue chromatographed on silica gel (eluent: heptanes/ethyl acetate 25:1 to 4:1)
  3. distillationdistilled under vacuum through a 20-cm Widmer column

Sources & evidence

ORD record
ord-c0a2831b9c9a43f59a52d7b21027b317
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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