Water → HCID 22708345, compound

HRID 1369012Notes

Reaction equation

HRID 1369012 reaction equation
O[Li].O.O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([C:17]([O:19]C)=[O:18])[OH:16]>C1COCC1>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][C:9]2([C:17]([OH:19])=[O:18])[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53646089HCID 53646089, compound

Product 1

HCID 22708345HCID 22708345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (0.19 g; 4.6 mmol) and water (4 mL) were added to a solution of 6-chloro-4-hydroxychroman-4-yl-carboxylic acid, methyl ester (0.56 g, 2.3 mmol; from step (i) above) in THF (6 mL). The reaction mixture was stirred at room temperature for 3 h, THF was evaporated and the water solution was washed with methylene chloride. The reaction mixture was acidified with HCl (2M) and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and evaporated, yielding a slowly crystallizing oil. Yield: 490 mg (93%).

Workup

  1. customTHF was evaporated
  2. washthe water solution was washed with methylene chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated
  6. customyielding
  7. customa slowly crystallizing oil

Sources & evidence

ORD record
ord-ca9c806b72054f9e99a894fae6adf986
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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