Water → HCID 18518693, compound

HRID 1369019Notes

Reaction equation

HRID 1369019 reaction equation
[OH-:1].[K+].O.[OH:4][C:5]1([C:18](N)=[O:19])[C:14]2[C:9](=[C:10]([Cl:17])[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[O:8][CH2:7][CH2:6]1>CC(O)C>[Cl:17][C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[C:14]2[C:9]=1[O:8][CH2:7][CH2:6][C:5]2([C:18]([OH:19])=[O:1])[OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18518706HCID 18518706, compound

Product 1

HCID 18518693HCID 18518693, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

KOH (1.2 g; 21 mmol) and water (25 mL) were added to a solution of 4-hydroxy-8-chloro-6-methoxychroman-4-yl-carboxylic amide (0.39 g; 1.5 mmol; from step (iv) above) in i-PrOH (25 mL). The reaction mixture was refluxed overnight, i-PrOH was evaporated and the water solution was washed with ether. The reaction mixture was acidified with HCl (2M) and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. Yield: 0.38 mg (97%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customi-PrOH was evaporated
  3. washthe water solution was washed with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-47f2c8197d584463813ebcabfab9aeec
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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