Formaldehyde → O-Cresol

HRID 2058336Notes

Reaction equation

HRID 2058336 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC[CH2:9]1.[CH3:14][OH:15].C=O.[H][H]>[Pd]>[C:6]1([CH3:9])[C:1]([OH:7])=[CH:2][CH:3]=[CH:4][CH:5]=1.[CH:6]1[C:1]([OH:7])=[CH:2][CH:3]=[C:4]([CH3:9])[CH:5]=1.[C:14]1([OH:15])[C:3]([CH3:2])=[CH:4][C:5]([CH3:9])=[CH:6][CH:1]=1

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 887MethanolHCID 996PhenolHCID 8082PiperidineHCID 178418361HCID 178418361, compound

Product 3

HCID 335O-CresolHCID 2879P-CresolHCID 77712,4-Dimethylphenol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
10 °C

Procedure

A mixture of phenol (94 grams, 1.0 moles), piperidine (43 grams, 0.5 mole), and methanol (50 moles) was cooled to 10° C. with agitation. Paraformaldehyde (15 grams, 0.5 mole) was added all at one time and the reaction temperature was maintained at 10° to 13° C. for 1.5 hours. The temperature was then allowed to rise to 25° C. The reaction mixture was heated to 85° C. and hydrogenated in a glass-lined autoclave in the presence of 1 gram of 5 percent palladium on carbon catalyst at a temperature of 120° to 130° C. for two hours at 120-150 psig of hydrogen. The product was filtered and the methanol in the filtrate removed by distillation. This left a product weighing 154 grams which, on analysis by gas chromatography (weight percent), contained the following: 37.5 percent phenol, 11.1 percent ortho-cresol, 14.6 percent para-cresol, and 0.7 percent 2,4-xylenol. This corresponds to yields of 40.6 percent for ortho-cresol, 53.3 percent for para-cresol, and 2.3 percent for 2,4-xylenol based on the phenol consumed.

Workup

  1. temperaturethe reaction temperature was maintained at 10° to 13° C. for 1.5 hours
  2. customto rise to 25° C
  3. filtrationThe product was filtered
  4. customthe methanol in the filtrate removed by distillation
  5. waitThis left a product

Sources & evidence

ORD record
ord-db77abc9815c44a2996bd8e550996880
Source dataset
uspto-grants-1980_07
Patent number
US04215229

Reaction notes

Loading…