Sodium Hydroxide → HCID 57804130, compound

HRID 2102917Notes

Reaction equation

HRID 2102917 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([C:13]#[C:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([C:13]#[C:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57804220HCID 57804220, compound

Product 1

HCID 57804130HCID 57804130, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 2-methoxy-4-(3,3-dimethylbut-1-ynyl)benzoate (1.10 g, 0.00447 mol), MeOH (20 mL), and 2N aqueous NaOH solution (5 mL) was stirred at 65° C. overnight. After allowing to cool, the mixture was concentrated under vacuum. The residue was treated with water, and extracted with hexane. The aqueous layer was acidified with 1N HCl to pH 2-3, and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2O4), filtered and concentrated under vacuum to give the product (870 mg, 84%) as a white solid. LC-MS: 3.22 min, 233.4 (M+1).

Workup

  1. temperatureto cool
  2. concentrationthe mixture was concentrated under vacuum
  3. additionThe residue was treated with water
  4. extractionextracted with hexane
  5. extractionextracted with EtOAc (50 mL×3)
  6. washThe combined organic layers were washed with brine
  7. customdried (Na2O4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01b850085f874fe7974cf7c8fb475301
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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