Hydrochloric Acid → HCID 87949617, compound

HRID 1060497Notes

Reaction equation

HRID 1060497 reaction equation
C[CH:2]([CH2:9][CH3:10])[CH2:3][C:4](=[N:7][OH:8])[CH2:5][CH3:6].N1C=CC=C[CH:12]=1.[C:17]1([O:27][CH3:28])[C:18](=[CH:20][CH:21]=[C:22]([CH:26]=1)[CH2:23][CH:24]=[CH2:25])[OH:19].Cl[C:30]([O-:32])=O.Cl>ClCCl>[CH2:23]([C:22]1[CH:21]=[CH:20][C:18]([O:19][C:30]([O:8][N:7]=[C:4]([CH2:3][CH2:2][CH2:9][CH3:10])[CH2:5][CH2:6][CH3:12])=[O:32])=[C:17]([O:27][CH3:28])[CH:26]=1)[CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 90787N-(5-Methyl-3-heptanylidene)hydroxylamineHCID 86757140HCID 86757140, compound

Product 1

HCID 87949617HCID 87949617, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution containing 7.47 g 5-methyl-heptan-3-one oxime and 6.33 g pyridine in 120 ml of dichloromethane was cooled to 5° C. Then, a solution of 13.00 g eugenol-chloroformate in 30 ml of dichloromethane was added to the solution and the resulting mixture was stirred for 68 hours at room temperature. Then, the mixture was acidified with aqueous hydrochloric acid, extracted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3, and brine. The organic phase was dried, filtered, and evaporated to dryness. The resulting oil was purified by distillation and chromatography to yield 13.26 g of a colorless oil.

Workup

  1. extractionextracted with ether
  2. washwashed with aqueous hydrochloric acid, saturated NaHCO3, and brine
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. distillationThe resulting oil was purified by distillation and chromatography

Sources & evidence

ORD record
ord-a63362863b6740178a73e7d5382bc694
Source dataset
uspto-grants-2003_02
Patent number
US06521797B1

Reaction notes

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