2,6-Dimethylphenol → Allyl 2,6-dimethylphenyl ether

HRID 2164896

Reaction equation

HRID 2164896 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C(=O)(OC)O[CH2:12][CH:13]=[CH2:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:14][CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 11776TriphenylphosphineHCID 534788Methyl 2-propen-1-yl carbonate

Product 1

HCID 641277Allyl 2,6-dimethylphenyl etherYield 98.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 2,6-dimethylphenol (1.22 g, 10 mmoles), allyl methyl carbonate (1.40 g, 12 mmoles), 5 percent palladium on charcoal (26 mg, 0.0125 mmole paladium) and triphenyl phosphine (20 mg, 0.0375 mmole) is heated at 70° C. for 45 minutes. Filtration of the catalyst and bulb-to-bulb distillation of the residue at 120° C., 10 mm Hg gives 1.60 g of substantially pure allyl 2,6-dimethylphenyl ether, 98.7 percent yield.

Workup

  1. filtrationFiltration of the catalyst and bulb-to-bulb distillation of the residue at 120° C.

Sources & evidence

ORD record
ord-e444575a45e546c887915ac2641f2e3f
Source dataset
uspto-grants-1985_03
Patent number
US04507492

Linked notes

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