Lithium hydroxide, monohydrate → HCID 66644015, compound

HRID 1474288Notes

Reaction equation

HRID 1474288 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14]([O-:16])=[O:15])[O:7][CH2:6][CH2:5]2.O[Li].O>CO.C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14]([OH:16])=[O:15])[O:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86647312HCID 86647312, compound

Product 1

HCID 66644015HCID 66644015, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate (12 g, 38 mmol) in 50 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (4.79 g, 114 mmol), and the mixture was stirred at ambient temperature overnight. The solvents were removed under vacuum, and to the residue was added 50 mL of water and the mixture was extracted with ether. The aqueous layer was then acidified with 4 N HCl to pH=3 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid.

Workup

  1. customThe solvents were removed under vacuum
  2. additionto the residue was added 50 mL of water
  3. extractionthe mixture was extracted with ether
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0977336ca2fc46ea93882a415aca4ea9
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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