Lithium Hydroxide → HCID 25128238, compound

HRID 1361076Notes

Reaction equation

HRID 1361076 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])[CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:19]([O:28][CH3:29])[CH:18]=1)[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:19]([O:28][CH3:29])[CH:18]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66971877HCID 66971877, compound

Product 1

HCID 25128238HCID 25128238, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.14 ml (0.85 mmol) of aqueous 1N lithium hydroxide solution are added to a solution of 259 mg (0.56 mmol) of methyl 3-{3-butoxy-4-[3-(4-butoxy-3-methoxyphenyl)propyl]phenyl}propanoate in 3 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 12 hours and then concentrated under vacuum. The residue is taken up in water, acidified by adding 1N hydrochloric acid solution and then extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. After trituration in heptane, 208 mg (83%) of 3-{3-butoxy-4-[3-(4-butoxy-3-methoxyphenyl)propyl]phenyl}propanoic acid are obtained in the form of white crystals with a melting point of 64° C.

Workup

  1. concentrationconcentrated under vacuum
  2. additionby adding 1N hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c61d5b37971f40febdfcb27e5a8f8217
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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