Sodium Hydroxide → HCID 22120010, compound

HRID 1274067Notes

Reaction equation

HRID 1274067 reaction equation
[Cl:1][C:2]1[C:14]([CH:15]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[O:16][CH3:17])=[C:13]([Cl:23])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:14]([CH:15]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[O:16][CH3:17])=[C:13]([Cl:23])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 22120011HCID 22120011, compound

Product 1

HCID 22120010HCID 22120010, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.3 g (6.4 mmol) of tert-butyl 2,4-dichloro-3-((2-furyl)(methoxymethyl))benzoate in 50 ml of methanol and 15 ml of water are heated under reflux with 0.7 g (16.1 mmol) of sodium hydroxide for 4 h. 5.0 ml of a 10% strength aqueous sodium hydroxide solution are added and the mixture is heated for a further 3 h. After the reaction mixture has been concentrated under reduced pressure, 50 ml of water are added and the reaction mixture is extracted with dichloromethane. The aqueous phase is acidified using 10% strength aqueous hydrochloric acid and the product is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield 1.8 g.

Workup

  1. temperaturethe mixture is heated for a further 3 h
  2. concentrationAfter the reaction mixture has been concentrated under reduced pressure, 50 ml of water
  3. additionare added
  4. extractionthe reaction mixture is extracted with dichloromethane
  5. extractionthe product is extracted with ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e6447d4f892f4450865fa304c3032dd4
Source dataset
uspto-grants-2000_12
Patent number
US06156702

Reaction notes

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