Acetic Acid → HCID 13020634, compound

HRID 1680869Notes

Reaction equation

HRID 1680869 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([Cl:18])[C:12]([CH3:17])([N+:14]([O-])=O)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])(=O)C.[Na+].C(O)(=O)C.C>[H][H].[Pt](=O)=O.COCCOC>[ClH:18].[CH3:17][C:12]([NH2:14])([CH3:13])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 517045Sodium AcetateHCID 13020595HCID 13020595, compound

Product 1

HCID 13020634HCID 13020634, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 80711,2-DimethoxyethaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 3.6 g of 1-(3,4-dimethoxyphenyl)-1-chloro-2-methyl-2-nitropropane, 910 mg of sodium acetate, 6.7 ml of acetic acid, 200 mg of platinum dioxide, 280 mg of activated charcoal and 35 ml of 1,2-dimethoxyethane is shaken at 60°-85° C. for 5.5 hours in hydrogen gas atmosphere under 55 atmospheric pressures. After cooling, insoluble materials are removed by filtration, and the filtrate is evaporated under reduced pressure to remove solvent. The residue (pale yellow oil) is dissolved in water, and then washed with ether. The aqueous layer is neutralized with 20% sodium hydroxide under cooling, and then extracted with ether. The extract is washed with water, dried and then evaporated to remove solvent. The residue (colorless oil) is converted into its hydrochloride with hydrogen chlorideether, and said hydrochloride is recrystallized from isopropylalcohol. 2.1 g of α,α-dimethyl-3,4-dimethoxyphenethylamine hydrochloride are thereby obtained as colorless plates.

Workup

  1. temperatureAfter cooling
  2. custominsoluble materials are removed by filtration
  3. customthe filtrate is evaporated under reduced pressure
  4. customto remove solvent
  5. dissolutionThe residue (pale yellow oil) is dissolved in water
  6. washwashed with ether
  7. temperatureunder cooling
  8. extractionextracted with ether
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated
  12. customto remove solvent
  13. customis recrystallized from isopropylalcohol

Sources & evidence

ORD record
ord-2c85ed82e4c2463db0d1e8aa4d57fd4a
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

Loading…