Hydrochloric Acid → HCID 54499309, compound

HRID 1384412Notes

Reaction equation

HRID 1384412 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[C:19]1([O:29][CH3:30])[C:20](=[CH:22][CH:23]=[C:24]([CH:28]=1)[CH2:25][CH:26]=[CH2:27])[OH:21].Cl[C:32]([O-])=[O:33].Cl>ClCCl>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:1][C:32](=[O:33])[O:21][C:20]2[CH:22]=[CH:23][C:24]([CH2:25][CH:26]=[CH2:27])=[CH:28][C:19]=2[O:29][CH3:30])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 777862-Hydroxy-1-(4-methoxyphenyl)ethanoneHCID 86757140HCID 86757140, compound

Product 1

HCID 54499309HCID 54499309, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 17.62 g of 2-hydroxy-4′-methoxyacetophenone (Kovach et al., J. Amer. Chem. Soc., Vol. 115, No. 23, (1993) p. 10476) and 12.96 g of pyridine in 240 ml of dichloromethane, a solution of 26.32 g of eugenol-chloroformate in 60 ml of dichloromethane was dropped in at 5-10° C. Then, the mixture was stirred for 6 hours at room temperature. The reaction mixture was then acidified with 2N HCl and extracted with ether. The combined organic phases were washed with 2N HCl, saturated sodium bicarbonate and brine, and then dried, filtered, and evaporated to dryness. The resulting solid was purified by recrystallization to yield 29.79 g of yellow crystals.

Workup

  1. extractionextracted with ether
  2. washThe combined organic phases were washed with 2N HCl, saturated sodium bicarbonate and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting solid was purified by recrystallization

Sources & evidence

ORD record
ord-d841b6e27acd447797caa918cceffa55
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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