Water → HCID 59760044, compound

HRID 1879126Notes

Reaction equation

HRID 1879126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([CH:26]=2)[C:15]([O:17]CC2C=CC=C(Cl)C=2)=[O:16])[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([CH:26]=2)[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 59760048HCID 59760048, compound

Product 1

HCID 59760044HCID 59760044, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-chlorophenyl)methyl 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoate from the preparation of Intermediate 84 described above (2.67 g, 6.66 mmol) in 1,4-dioxane (20 ml) and water (10 ml) was treated with lithium hydroxide (419 mg, 9.99 mmol, 1.5 eq). The resulting mixture was stirred at room temperature under argon overnight. A further portion of lithium hydroxide (419 mg, 9.99 mmol, 1.5 eq) was added and stirring continued at room temperature for 2 hours. Stirring continued at room temperature overnight. The solvent was then evaporated to dryness and then partitioned between 2M HCl (100 ml) and diethylether (100 ml). The organic layer was separated and passed through a hydrophobic frit to remove any water and evaporated to dryness to afford the title compound as a white solid (1.98 g) (contains 12% impurity). No further purification carried out. MS (ES−) m/z 275 [M−H]− (C15H1335ClO3).

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 2 hours
  3. stirringStirring
  4. waitcontinued at room temperature overnight
  5. customThe solvent was then evaporated to dryness
  6. custompartitioned between 2M HCl (100 ml) and diethylether (100 ml)
  7. customThe organic layer was separated
  8. customto remove any water
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-f5b1f8430412479eb4de1853217170be
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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