4-Hydroxybenzaldehyde → 4-(Allyloxy)benzaldehyde

HRID 2164894Notes

Reaction equation

HRID 2164894 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.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]>[CH2:14]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 534788Methyl 2-propen-1-yl carbonate

Product 1

HCID 959424-(Allyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of p-hydroxybenzaldehyde (4.0 g, 33 mmoles), allyl methyl carbonate (16.0 g, 138 mmoles), 5 percent palladium on charcoal (1.3 g, 0.6 mmole palladium) and triphenyl phosphine (0.086 g, 0.32 mmole) is refluxed overnight. After removal of the catalyst and distillation (90° C., 0.6 mm Hg), 4.54 g, 85 percent of substantially pure p-allyloxybenzaldehyde is obtained.

Workup

  1. temperatureis refluxed overnight
  2. customAfter removal of the catalyst and distillation (90° C., 0.6 mm Hg), 4.54 g, 85 percent of substantially pure p-allyloxybenzaldehyde
  3. customis obtained

Sources & evidence

ORD record
ord-4e963cdf97e744098b9380c35a1c0e1f
Source dataset
uspto-grants-1985_03
Patent number
US04507492

Reaction notes

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