Hydrochloric Acid → HCID 86737802, compound

HRID 1680495Notes

Reaction equation

HRID 1680495 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Cl.[N:13]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH2:22]([O:24][C:25](=[O:31])[CH2:26][C:27](=[O:30])[CH2:28][CH3:29])[CH3:23].[OH-].[K+]>O.CO>[CH2:22]([O:24][C:25](=[O:31])[CH2:26][C:27](=[O:30])[CH:28]([CH3:29])[N:13]=[N:9][C:8]1[CH:10]=[CH:11][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=1)[CH3:23]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 78656Ethyl 3-oxovalerateHCID 808922-(4-Aminophenoxy)ethanolHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 86737802HCID 86737802, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

65.4 g of 4-(β-hydroxyethoxy)-aniline, mixed with 70 ml of strong hydrochloric acid and 78 g of ice, are diazotized with stirring at 0° C. with a solution of 22.1 g of sodium nitrite in 50 ml of water. The reaction mixture is stirred for 1 h, whereupon 33 g of sodium acetate are added. The obtained diazonium solution is then added to a mixture made of a solution of 47.5 g of α-methylacetylacetic acid ethyl ester in 300 ml of methanol, 300 g of ice and a solution of 21.8 g of potassium hydroxide in 30 ml of water. The whole is stirred at about 5° C. for 4 h and extracted with toluene. The extract is washed with water, dried and evaporated in a rotary evaporator. The residual 65 g of oil are directly further transformed without purification.

Workup

  1. additionare added
  2. extractionextracted with toluene
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated in a rotary evaporator
  6. customThe residual 65 g of oil are directly further transformed without purification

Sources & evidence

ORD record
ord-4d708ef149f849219ac9cf55f394acaf
Source dataset
uspto-grants-1981_06
Patent number
US04273855

Reaction notes

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