Methanol → 4-Hydroxybenzyl Alcohol

HRID 259796Notes

Reaction equation

C[C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C[O-].[Na+].CO>[Pd]>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:2][OH:3])=[CH:5][CH:6]=1

Participants

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

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

Sources & evidence

ORD record: ord-d815648d6320437f877cfb39ee04bfab
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523378

Reaction notes

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