Tetrahydrofuran → 2-Chloro-4-(3,3-dimethylbut-1-ynyl)benzoic acid

HRID 2102931Notes

Reaction equation

HRID 2102931 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57804186HCID 57804186, compound

Product 1

HCID 578041752-Chloro-4-(3,3-dimethylbut-1-ynyl)benzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-chloro-4-(3,3-dimethylbut-1-ynyl)benzoate (330 mg, 0.0013 mol), 2N aq. NaOH (3.0 mL), THF (5 mL), and MeOH (5 mL) was stirred at rt for 5 h. The mixture was concentrated under vacuum and the residue was treated with water and acidified with 1N HCl to pH 2-3, and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under vacuum to give the product (305 mg, 98%) as a white solid. tR=3.56 min, 234.9 & 236.9 (M−1).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue was treated with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-042bfefd9fa24c5db6c95ac365733173
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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