Lithium hydroxide, monohydrate → HCID 22282647, compound

HRID 2085344Notes

Reaction equation

HRID 2085344 reaction equation
O.[OH-].[Li+].[O:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)=[CH:6][CH2:5]1>O.C1COCC1.CO>[O:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=2)=[CH:6][CH2:5]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22282577HCID 22282577, compound

Product 1

HCID 22282647HCID 22282647, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide hydrate (0.80 g, 19.0 mmol) dissolved in water (20 mL) was added to a solution of methyl 4-(2H-chromen-4-yl)benzoate from reaction 34b (1.5 gm, 5.7 mmol) in THF (20 mL) and methanol (20 mL) under nitrogen atmosphere at room temperature. The reaction was heated to 50° C. for 2 h, allowed to cool, concentrated then partitioned between 1 N HCl and ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give 4-(2H-chromen-4-yl)benzoic acid (1.29 g, 89%) as a tan solid. MS found: (M−H)+=251.

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. customthen partitioned between 1 N HCl and ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1fab104a4ebb4cd4805a126f6708acfa
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

Loading…