Dimethylamine → 6-tert-Butyl-4-[(dimethylamino)methyl]-2,3-dimethylphenol

HRID 838836Notes

Reaction equation

HRID 838836 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][NH:15][CH3:16].[CH2:17]=O>C1(C)C=CC=CC=1.CCOCC>[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]([CH2:14][N:15]([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 170766Phenol, 6-(1,1-dimethylethyl)-2,3-dimethyl-

Product 1

HCID 221015906-tert-Butyl-4-[(dimethylamino)methyl]-2,3-dimethylphenol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To 142.4 grams of 6-tert.-butyl-2,3-dimethylphenol dissolved in 270 ml of toluene was added 144.4 grams of a 25% aqueous solution of dimethylamine at about room temperature. 65.7 grams of 36.5% aqueous formaldehyde was then added over a ten minute period to the reaction mixture initially at 15°, the temperature rising to 30° at the end of the addition. The reaction mixture was then warmed to 40° for 3 hours and finally heated at reflux (85°) for 2 hours. The reaction was diluted with about 1 liter of ether and the aqueous layer separated, the upper ether layer being washed three times with water. After drying over sodium sulfate, the organic phase was stripped to dryness at reduced pressures yielding 176.3 grams of crude product. The crude product was crystallized from heptane, yielding white cyrstals melting at 101° to 104°.

Workup

  1. additionthe temperature rising to 30° at the end of the addition
  2. temperatureThe reaction mixture was then warmed to 40° for 3 hours
  3. temperaturefinally heated
  4. temperatureat reflux (85°) for 2 hours
  5. customthe aqueous layer separated
  6. washthe upper ether layer being washed three times with water
  7. dry with materialAfter drying over sodium sulfate

Sources & evidence

ORD record
ord-a06835b690c044a9b20c2da90b4be29b
Source dataset
uspto-grants-1978_06
Patent number
US04093587

Reaction notes

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