Lithium Hydroxide → HCID 28830843, compound

HRID 1623650Notes

Reaction equation

HRID 1623650 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]=[C:26]([O:30][CH3:31])[CH:25]=2)=[C:8]([CH:21]=1)[C:9]([O:11]CC1C=CC=C(OC)C=1)=[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]=[C:26]([O:30][CH3:31])[CH:25]=2)=[C:8]([CH:21]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107679HCID 67107679, compound

Product 1

HCID 28830843HCID 28830843, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of lithium hydroxide (395 mg, 9.40 mmol) in water (20 ml) was added dropwise to a stirred solution of [3-(methyloxy)phenyl]methyl 5-bromo-2-({[3-(methyloxy)phenyl]methyl}oxy)benzoate (may be prepared as described in Description 29; 430 mg, 0.94 mmol) in THF (20 ml) 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). The aqueous phase was then extracted with ethyl acetate (3×20 ml). The organic phase was evaporated in vacuo to yield the title compound as a light yellow solid. 275 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 evaporated in vacuo

Sources & evidence

ORD record
ord-6253feb1efc6431882349dde80c2c078
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…