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

HRID 1658034Notes

Reaction equation

HRID 1658034 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 dissoled 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 10 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 crystals 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
  8. customyielding 176.3 grams of crude product
  9. customThe crude product was crystallized from heptane

Sources & evidence

ORD record
ord-9458e18bdd204ee9acf7d1ab025e4450
Source dataset
uspto-grants-1976_06
Patent number
US03962377

Reaction notes

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