Water → HCID 22731986, compound

HRID 1369013Notes

Reaction equation

HRID 1369013 reaction equation
O[Li].O.O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([C:18]([O:20]C)=[O:19])[OH:17]>C1COCC1>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([C:18]([OH:20])=[O:19])[OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 131722784HCID 131722784, compound

Product 1

HCID 22731986HCID 22731986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (0.15 g; 3.6 mmol) and water (2 mL) were added to a solution of 6,8-dichloro-4hydroxychroman-4yl-carboxylic acid, methyl ester (0.50 g; 1.8 mmol; from step (i) above) in THF (5 mL). The resultant mixture was stirred at room temperature for 30 min., THF was evaporated and the water phase was washed with methylene chloride. The reaction mixture was made acidic with HCl (2M) and extracted with methylene chloride. The organic layer was dried (Na2SO4) and evaporated, yielding the sub-title compound. Yield: 390 mg (83%).

Workup

  1. customTHF was evaporated
  2. washthe water phase was washed with methylene chloride
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-91a30130c12947c69f931a28a928305a
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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