Lithium Hydroxide → HCID 25128237, compound

HRID 1361074Notes

Reaction equation

HRID 1361074 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[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][CH3:25])=[C:19]([O:26][CH3:27])[CH:18]=1)[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[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][CH3:25])=[C:19]([O:26][CH3:27])[CH:18]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66971622HCID 66971622, compound

Product 1

HCID 25128237HCID 25128237, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

ml (1.1 mmol) of aqueous 1N lithium hydroxide solution are added to a solution of 240 mg (0.56 mmol) of methyl 3-{3-butoxy-4-[3-(4-ethoxy-3-methoxyphenyl)propyl]phenyl}propanoate in 3 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 12 hours. The reaction medium is concentrated and then taken up in water and acidified by addition of aqueous hydrochloric acid solution and then extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate and filtered. The solvents are evaporated off. After recrystallization of the residue obtained from 6 ml of cyclohexane, 184 mg (79%) of 3-{3-butoxy-4-[3-(4-ethoxy-3-methoxyphenyl)propyl]phenyl}propanoic acid are obtained in the form of a white solid with a melting point of 66° C.

Workup

  1. concentrationThe reaction medium is concentrated
  2. additionacidified by addition of aqueous 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. customThe solvents are evaporated off
  8. customAfter recrystallization of the residue

Sources & evidence

ORD record
ord-8472aa13081e4d03a82646ab6c8a72da
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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