Ethanolamine → HCID 14391205, compound

HRID 1381529Notes

Reaction equation

HRID 1381529 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[OH:11])=O)=[CH:4][CH:3]=1.[CH2:19]([CH2:21][NH2:22])[OH:20].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[BH4-].[Na+].C(Cl)(Cl)[Cl:40]>C(O)C>[ClH:40].[OH:20][CH2:19][CH2:21][NH:22][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[OH:11]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 6212ChloroformHCID 14812Phosphorus oxide (P4O10)HCID 2248484,4'-DIMETHYLBENZOINHCID 4311764Sodium borohydride

Product 1

HCID 14391205HCID 14391205, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 40.0 g (0.33 mole) of tolualdehyde, 10 ml ethanol and 10.84 g (0.17 mole) of potassium cyanide was refluxed overnight at 90° C. An additional 10.8 g (0.17 mole) of potassium cyanide was added and the mixture was refluxed for 5 hr more. Aqueous sodium bisulfite was added to remove unreacted aldehyde. The mixture was reheated, cooled and extracted with methylene chloride. The solvent was stripped off. On dissolving the residue in isopropyl alcohol, crystals were obtained in amount of 14.26 g which represents a 35% yield of 4,4'-dimethylbenzoin. A portion of the 4,4'-dimethylbenzoin, 4.74 g (0.19 mole), 3.84 g (0.063 mole) of ethanolamine and 2.5 g (0.018 mole) of phosphorus pentoxide were mixed and heated under nitrogen atmosphere by means of an oil bath for 4 hr at 105° C. The reaction mixture was cooled and 100 ml of chloroform was added to it with mixing. The chloroform layer was separated and washed twice with 100 ml of dilute hydrochloric acid each time. The aqueous layers were combined, basified and washed with chloroform. The chloroform layer was separated, concentrated and dissolved in 100 ml of ethanol to which 0.038 mole of sodium borohydride in aqueous solution was added. The mixture was stirred for 2 hr and concentrated to dryness. The residue was partitioned between 100 ml of 25% sodium hydroxide and 100 ml of methylene chloride. The methylene chloride layer was washed twice with 100 ml of water each time, concentrated and the residue was dissolved in hot isopropyl alcohol. A solution of hydrogen chloride in isopropyl alcohol was added to give, after filtration and drying, 1.25 g (48.8%) of the hydrochloride salt, m.p. 217°-220° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionwith mixing
  3. customThe chloroform layer was separated
  4. washwashed twice with 100 ml of dilute hydrochloric acid each time
  5. washwashed with chloroform
  6. customThe chloroform layer was separated
  7. concentrationconcentrated
  8. additionwas added
  9. concentrationconcentrated to dryness
  10. customThe residue was partitioned between 100 ml of 25% sodium hydroxide and 100 ml of methylene chloride
  11. washThe methylene chloride layer was washed twice with 100 ml of water each time
  12. concentrationconcentrated
  13. dissolutionthe residue was dissolved in hot isopropyl alcohol
  14. additionA solution of hydrogen chloride in isopropyl alcohol was added
  15. customto give
  16. filtrationafter filtration
  17. customdrying

Sources & evidence

ORD record
ord-d23738c82c754e4ea008924aaaa94889
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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