Acetone → Phenol, 4-[(1-methylethyl)amino]-

HRID 463537Notes

Reaction equation

HRID 463537 reaction equation
[CH:1]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[CH3:11][C:12]([CH3:14])=O.[H][H]>[Pt]=O>[CH:12]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:10])=[CH:2][CH:1]=1)([CH3:14])[CH3:11]

Participants

5

Reactant 3

HCID 180AcetoneHCID 9804-NitrophenolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 301439Phenol, 4-[(1-methylethyl)amino]-Yield 41%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

Twenty-five g (0.18 moles) of p-nitrophenol and 58 g (1 mole) of acetone were mixed together and catalytically reduced using hydrogen and platinum oxide until hydrogen was no longer taken up. The work-up followed the procedure of Majors (J. Amer. Chem. Soc. 31:1901-1908 (1931), giving 11 g (41%) of N-isopropyl-p-hydroxyaniline, m.p. 143° C.

Sources & evidence

ORD record
ord-ac279cd664854482b4cf8ee278aae26d
Source dataset
uspto-grants-1985_05
Patent number
US04520134

Reaction notes

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