Hydrochloric Acid → HCID 54366716, compound

HRID 1031686Notes

Reaction equation

HRID 1031686 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:20]([CH3:22])=[O:21].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:28]=O.[OH-].[Na+].Cl>CO.O.C(OCC)(=O)C>[OH:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:20]([CH:22]=[CH:28][C:27]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=1)=[O:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 14798Sodium HydroxideHCID 10734538HCID 10734538, compound

Product 1

HCID 54366716HCID 54366716, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 25 ml of methanol were suspended 2.0 g of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone and 1.03 g of 3,4-dimethoxybenzaldehyde. Thereto was added 5 ml of 50% aqueous sodium hydroxide. The mixture was stirred for 3 hours at room temperature. The reaction mixture was introduced into a mixture of 20 ml of ethyl acetate and 20 ml of water. The resulting mixture was adjusted to pH 2.0 with 4N hydrochloric acid. The resulting crystal was collected by filtration, washed with water and ethyl acetate in this order, and recrystallized from acetic acid to obtain 2.2 g (yield: 75.6%) of 2-(3,4-dimethoxyphenyl)vinyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone.

Workup

  1. filtrationThe resulting crystal was collected by filtration
  2. washwashed with water and ethyl acetate in this order
  3. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-c203daf487ee4cbbb0c09b6240df2af8
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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