Lithium Hydroxide → HCID 28880573, compound

HRID 1623638Notes

Reaction equation

HRID 1623638 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][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC(OC)=CC=1)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107142HCID 67107142, compound

Product 1

HCID 28880573HCID 28880573, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (367 mg, 8.75 mmol) in water (20 ml) was added dropwise to a stirred solution of [4-(methyloxy)phenyl]methyl 5-bromo-2-({[4-(methyloxy)phenyl]methyl}oxy)benzoate (may be prepared as described in Description 17; 400 mg, 0.875 mmol) in THF over 1 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) and was extracted with ethyl acetate (3×20 ml). The organic phase was evaporated in vacuo to yield the title compound as a light yellow solid. 200 mg.

Workup

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

Sources & evidence

ORD record
ord-62f8e890f0074e3999df32bd8309f07b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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