Benzene → HCID 21432285, compound

HRID 268422Notes

Reaction equation

HRID 268422 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].C1C=CC=CC=1.[CH3:18][NH:19][CH3:20].[CH2:21]=O>O>[CH3:18][N:19]([CH2:10][C:4]1[C:5]([CH3:9])=[C:6]([OH:7])[C:8]([CH3:21])=[C:2]([CH3:1])[C:3]=1[OH:11])[CH3:20]

Participants

6

Reactant 4

HCID 241BenzeneHCID 674DimethylamineHCID 712FormaldehydeHCID 12785Trimethylhydroquinone

Product 1

HCID 21432285HCID 21432285, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trimethylhydroquinone (7.61 g.) was suspended under N2 in 60 ml. of benzene and 15 ml. of 25% dimethylamine in H2O. Aqueous formaldehyde solution (37%, 7.5 ml.) was added over 15 minutes and stirring was continued at 25° overnight. The benzene layer was washed with H2O, dried over Na2SO4, and stripped of solvent to give 2-dimethylaminomethyl-3,5,6-trimethylhydroquinone as a light tan solid. A similarly prepared sample of this material, which is quite susceptible to air oxidation, had a m.p. of 103°-108.5° with decomposition, after isolation from methanol-H2O.

Workup

  1. washThe benzene layer was washed with H2O
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-5b0bf85526cf461b873b0dadc7c07a2b
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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