Sodium Hydroxide → 2-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acid

HRID 1456824Notes

Reaction equation

HRID 1456824 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([O:29]C)=[O:28])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([OH:29])=[O:28])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22107203Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

Product 1

HCID 221072002-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acidYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2 -(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate (0.26 g) in MeOH (10.0 ml) was added 10% aqueous NaOH (2.0 ml), and the reaction mixture was heated under reflux for 6 hr. After removal of solvent, the aqueous layer was washed with Et2O. The solution was adjusted to pH 2.0 with 10% aqueous HCl, and extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1) to give the title compound (0.20 g) as violet crystals; mp 168°-169° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customAfter removal of solvent
  4. washthe aqueous layer was washed with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1)

Sources & evidence

ORD record
ord-233133649e0b4c0896354c5153be05f6
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

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