Lithium Hydroxide → (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid

HRID 602277Notes

Reaction equation

HRID 602277 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.[OH-].[Li+]>CO.C1COCC1.O.O>[Cl:20][C:16]1[CH:15]=[C:14](/[CH:13]=[CH:12]/[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=2[C:3]([OH:21])=[O:2])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 596842572-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester

Product 1

HCID 59684233(E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Crude 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester was suspended in methanol:THF:water (3:1:1 [v/v], 400 mL) and lithium hydroxide (12.10 g, 289 mmol) added. The mixture was stirred for 22 h at ambient temperature and concentrated in vacuo to give a pale brown solid. The crude product was re-dissolved in water (400 mL), the solution washed with diethyl ether (3×250 mL) and acidified to pH 2 with 1 N HCl (aq.). The aqueous was extracted with ethyl acetate (3×200 mL), the organic phase dried (MgSO4) and concentrated in vacuo to give a tan solid which was triturated with methanol and filtered to give (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid (15.43 g, 53.44 mmol, 74% for 2 steps from 2-bromo-5-methoxybenzoic acid methyl ester) as an off-white powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a pale brown solid
  3. washthe solution washed with diethyl ether (3×250 mL)
  4. extractionThe aqueous was extracted with ethyl acetate (3×200 mL)
  5. dry with materialthe organic phase dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a tan solid which
  8. customwas triturated with methanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6c8c1d0152d24dde9c988adf45e65b00
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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