Valeryl chloride → HCID 66688801, compound

HRID 245343Notes

Reaction equation

HRID 245343 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[K].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:21]>CC(C)=O>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:21])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 666879802-(2-Hydroxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone potassium salt

Product 1

HCID 66688801HCID 66688801, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.23 g (35.0 mmol) of valeroyl chloride (compound of the formula VI) were added with cooling at −10° C. to 20° C. to a stirred suspension of 11.3 g (34.7 mmol) of 2-(2-hydroxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone potassium salt (example 1) in 50 ml of dry acetone. After 30 minutes the reaction was complete, as monitored by LC-MS, and the mixture was filtered through a layer of Celite to remove the precipitated potassium chloride. The solution was evaporated to dryness to give 9.23 g (98%) of a yellow oil which slowly crystallized while standing at room temperature.

Workup

  1. filtrationthe mixture was filtered through a layer of Celite
  2. customto remove the precipitated potassium chloride
  3. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-835ecdb5ca6140f49b0b9dc67f9d4e95
Source dataset
uspto-grants-2014_02
Patent number
US08658808B2

Reaction notes

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