Lithium hydroxide, monohydrate → HCID 53330617, compound

HRID 2042920Notes

Reaction equation

HRID 2042920 reaction equation
C([O:4][CH2:5][C:6]1[C:15]([Cl:16])=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[C:8]([Br:17])[CH:7]=1)(=O)C.O.[OH-].[Li+]>C1COCC1.CO.O>[Br:17][C:8]1[CH:7]=[C:6]([CH2:5][OH:4])[C:15]([Cl:16])=[CH:14][C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53330277HCID 53330277, compound

Product 1

HCID 53330617HCID 53330617, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of acetate 27 (33.5 g, 104.1 mmol) in THF/MeOH/H2O (250 mL/250 mL/90 mL) was added lithium hydroxide monohydrate (13.1 g, 312 mmol). The mixture was stirred at room temperature for 15 h. The mixture was evaporated in vacuo to remove organic solvents. The residue was diluted with H2O, cooled to 0° C. and acidified with aq. 1 N HCl solution. The titled compound 28 was precipitated as a solid, filtered off and washed with H2O. The solid was dried under vacuum at 50° C. for 15 h to obtain the product (27.2 g, 96%). MH+265.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto remove organic solvents
  3. additionThe residue was diluted with H2O
  4. temperaturecooled to 0° C.
  5. customThe titled compound 28 was precipitated as a solid
  6. filtrationfiltered off
  7. washwashed with H2O
  8. customThe solid was dried under vacuum at 50° C. for 15 h

Sources & evidence

ORD record
ord-ca22ec8a6a7945c18b9ca9827e63da2b
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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