Methanol → Cyclohexanol, 4-(1,1,3,3-tetramethylbutyl)-

4-t-octylphenol (250 g, used as received from Rohm and Haas), methanol (250 ml), acetic acid (2.5 ml) and rhodium on carbon catalyst (5.0 g, 5% rhodium, MCB Chemicals) were added to a 3 L glass lined autoclave. The autoclave was charged to 60 psig H2 and heated at 60° C. until hydrogen uptake was complete (about 10 hrs.). The mixture was cooled to room temperature and the catalyst was removed by filtration in a glove bag under a nitrogen atmosphere (CAUTION: pyrophoric catalyst). The solvent was removed on a rotary evaporator and the residue was dissoved in dichloromethane and extracted with 10% sodium carbonate solution (3×250 ml) to remove phenolic contamination, thus avoiding the formation of a yellow impurity in the subsequent oxidation step. The dichloromethane solution was washed with 25% sulfuric acid (2×100 ml) distilled water (1×250 ml), and dried over anhydrous magnesium sulfate, after which the solvent was evaporated to isolate 4-t-octylcyclohexanol as a low melting off-white solid (182 g, 81%).

1. additionThe autoclave was charged to 60 psig H2
2. custom(about 10 hrs.)
3. customthe catalyst was removed by filtration in a glove bag under a nitrogen atmosphere (CAUTION: pyrophoric catalyst)
4. customThe solvent was removed on a rotary evaporator
5. extractionextracted with 10% sodium carbonate solution (3×250 ml)
6. customto remove phenolic contamination
7. washThe dichloromethane solution was washed with 25% sulfuric acid (2×100 ml)
8. distillationdistilled water (1×250 ml)
9. dry with materialdried over anhydrous magnesium sulfate
10. customafter which the solvent was evaporated

ORD record

ord-7a6c8232f8e94fa7976dca173e2792fe

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876046