Lithium Hydroxide → HCID 60711769, compound

HRID 1623652Notes

Reaction equation

HRID 1623652 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC=CC=1OC)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67106970HCID 67106970, compound

Product 1

HCID 60711769HCID 60711769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (385 mg, 9.18 mmol) in water (20 ml) was added dropwise to a stirred solution of [2-(methyloxy)phenyl]methyl 5-bromo-2-({[2-(methyloxy)phenyl]methyl}oxy)benzoate (may be prepared as described in Description 31; 420 mg, 0.92 mmol) in THF (20 ml) over 5 min. The reaction mixture was stirred at 20° C. for 16 h. The organic phase was evaporated and the aqueous phase (20 ml) was extracted with ethyl acetate (20 ml). The aqueous phase (20 ml) was adjusted to pH 2 with 2M hydrochloric acid (1 ml). The aqueous phase was then extracted with ethyl acetate (3×20 ml). The organic phase was then evaporated in vacuo to yield the title compound as a light yellow solid. 280 mg.

Workup

  1. customThe organic phase was evaporated
  2. extractionthe aqueous phase (20 ml) was extracted with ethyl acetate (20 ml)
  3. extractionThe aqueous phase was then extracted with ethyl acetate (3×20 ml)
  4. customThe organic phase was then evaporated in vacuo

Sources & evidence

ORD record
ord-779e44b0671b45b7bcea42e663a072eb
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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