Methacryloyl chloride → HCID 22964457, compound

HRID 1086912Notes

Reaction equation

HRID 1086912 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1.[OH-].[Na+].[C:24](Cl)(=[O:28])[C:25]([CH3:27])=[CH2:26]>O.C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26])=[CH:7][CH:8]=2)[C:3]=1[N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1

Participants

6

Reactant 3

HCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 53736875HCID 53736875, compound

Product 1

HCID 22964457HCID 22964457, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of BDHN or 2(2,7-dihydroxynaphthyl) 2H-benzotriazole (5.0 g 18 m mol) and NaOH (0.8 g, 20 m mol) in water (100 ml) a solution of methacryloyl chloride (20 m mol, 4 ml) in chloroform (50 ml) was added dropwise with vigorous stirring. The mixture was stirred for 1 additional hour. The organic layer was separated and washed thoroughly with water before evaporation to yield a crude product that was recrystallized from carbon tetrachloride to give a yellow solid (2.5 g, 40% yield) of 2(2-hydroxy-7-methacryloxynaphthyl) 2H-benzotriazole--m.p. 167°-168° C.

Workup

  1. customThe organic layer was separated
  2. washwashed thoroughly with water before evaporation
  3. customto yield a crude product that
  4. customwas recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-5c92a1608a9b4fc587fde66eccf4e8e7
Source dataset
uspto-grants-1991_07
Patent number
US05032657

Reaction notes

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