Sodium Hydroxide → DR 3438

HRID 1905085Notes

Reaction equation

HRID 1905085 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:20][CH2:21][C:22]([OH:24])=[O:23])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14254503ethyl {[5-chloro-3-(2-methylphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetate

Product 1

HCID 196673DR 3438Yield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1.2 l of ethanol was suspended 132 g of ethyl {[5-chloro-3-(2-methylphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetate, and 0.53 l of a 1N sodium hydroxide aqueous solution was slowly added dropwise to the suspension at room temperature, followed by stirring at room temperature for 3 hours. The insoluble material was removed by filtration, and the filtrate was acidified with hydrochloric acid while ice-cooling and stirring. The stirring was continued at room temperature overnight. The precipitated crystals were collected by filtration, washed with water, and dried to obtain 105 g of the entitled compound having a melting point of 191° to 192° C.

Workup

  1. additionwas slowly added dropwise to the suspension at room temperature
  2. customThe insoluble material was removed by filtration
  3. temperaturecooling
  4. stirringstirring
  5. waitThe stirring was continued at room temperature overnight
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-82ae7a74b9b64955ba6b7d3ae3080f79
Source dataset
uspto-grants-1989_06
Patent number
US04841076

Reaction notes

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