Methanol → Tyrosol

HRID 864685Notes

Reaction equation

HRID 864685 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=O.C[O-:12].[Na+].CO>[Pd]>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:2][CH2:1][OH:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 74694'-HydroxyacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 10393Tyrosol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
45 °C

Procedure

To a five-gallon stainless steel reactor, a solution of 4-hydroxyacetophenone (2500 g, 18.4 moles) and a 25% solution of sodium methoxide in methanol (39.1 g, 0.26 moles) in methanol (10,000 g, 312.5 moles), and palladium on carbon catalyst (ESCAT 10, 125 g) were charged. The reactor is purged three times with nitrogen (100 psi). Hydrogen is then charged to a pressure of 300 psi and the reactor is heated to 45° C. The temperature is maintained at 45° C. for three hours at a constant hydrogen pressure of 500 psi. The reactor is cooled to 30° C. and then discharged (12,245 g). The analysis of the solution gave a conversion of 97.6% and a selectivity of 96.0% (note Table 2).

Workup

  1. customThe reactor is purged three times with nitrogen (100 psi)
  2. additionHydrogen is then charged to a pressure of 300 psi
  3. temperatureThe temperature is maintained at 45° C. for three hours at a constant hydrogen pressure of 500 psi
  4. temperatureThe reactor is cooled to 30° C.
  5. customThe analysis of the solution gave a conversion of 97.6%

Sources & evidence

ORD record
ord-b7e7a5e5a1bc475e8ca6eaca8bc69c6c
Source dataset
uspto-grants-1996_10
Patent number
US05563300

Reaction notes

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