Hydrochloric Acid → HCID 57083774, compound

HRID 1679779Notes

Reaction equation

HRID 1679779 reaction equation
[CH3:1][O-].[Na+].C[C:5](C)([C:9]([O-:11])=[O:10])[C:6]([O-:8])=O.[C:13]([C:17]1[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH2:26]N(C)C)[CH:18]=1)([CH3:16])([CH3:15])[CH3:14].Cl.CN(C)[CH:33]=[O:34]>C(Cl)(Cl)Cl>[C:13]([C:17]1[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH:18]=1)[CH2:26][CH:5]([C:6]([O:34][CH3:33])=[O:8])[C:9]([O:11][CH3:1])=[O:10])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6946994DimethylmalonatHCID 10942334Sodium MethoxideHCID 221015906-tert-Butyl-4-[(dimethylamino)methyl]-2,3-dimethylphenol

Product 1

HCID 57083774HCID 57083774, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

1.08 Grams of sodium methylate (0.02 moles) was added to 26.4 grams of dimethylmalonate (0.20 moles) in 25 ml of dry dimethylformamide in a nitrogen atmosphere and warmed to 40° C to obtain a clear solution. 47 grams of 6-tert.-butyl-2,3-dimethyl-4-(dimethylaminomethyl)phenol (0.20 moles) was added at room temperature, the reaction mixture becoming blue and was then gradually heated to 40° C over a period of about 40 minutes during which the blue color disappeared. The reaction mixture was then heated at 80° C for 13/4 hours. After acidification with 6N aqueous hydrochloric acid, the reaction mixture was poured into 200 ml of an ice-water dispersion with stirring to yield a hard crystalline precipitate. This precipitate was taken up in 700 ml of chloroform, the chloroform solution washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate and finally with water again. After drying over anhydrous sodium sulfate and filtering free of drying agent, the solvent was removed by distillation at reduced pressures. Crystallization of the residue from 1,2-dichloroethane yielded the product as white crystals melting at 140° to 143° C.

Workup

  1. customto obtain a clear solution
  2. temperaturewas then gradually heated to 40° C over a period of about 40 minutes during which the blue color
  3. temperatureThe reaction mixture was then heated at 80° C for 13/4 hours
  4. customto yield a hard crystalline precipitate
  5. washthe chloroform solution washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate and finally with water again
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. filtrationfiltering free
  8. customof drying agent
  9. customthe solvent was removed by distillation at reduced pressures
  10. customCrystallization of the residue from 1,2-dichloroethane

Sources & evidence

ORD record
ord-e6df329100e34831af7cb73f4cc318ce
Source dataset
uspto-grants-1978_03
Patent number
US04081475

Reaction notes

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