Sodium Hydroxide → 3-Methyl-2-(2-methyl-1-propenyl)benzoic acid

HRID 1047902Notes

Reaction equation

HRID 1047902 reaction equation
C([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH:12]=[C:13]([CH3:15])[CH3:14])C.[OH-].[Na+]>CO>[CH3:11][C:7]1[C:6]([CH:12]=[C:13]([CH3:15])[CH3:14])=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:16])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59314297HCID 59314297, compound

Product 1

HCID 593140863-Methyl-2-(2-methyl-1-propenyl)benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the 3-methyl-2-(2-methyl-1-propenyl)benzoic acid ethyl ester (290) (3 g-0.014 mol) in MeOH (50 mL) is treated with 2N NaOH (10 mL) and refluxed for 6 h. The solvent is removed in vacuo and the residue diluted with water (75 mL). The aqueous phase is extracted with EtOAc (30 mL) and then separated and acidified to pH 2-3 with concentrated HCl. The solid precipitated is extracted into EtOAc (3×50 mL). The extracts are washed with water (2×30 mL) and brine (2×30 mL), and dried over MgSO4 and concentrated in vacuo to give the product as white solid (2.0 g, 75%).

Workup

  1. temperaturerefluxed for 6 h
  2. customThe solvent is removed in vacuo
  3. additionthe residue diluted with water (75 mL)
  4. extractionThe aqueous phase is extracted with EtOAc (30 mL)
  5. customseparated
  6. customThe solid precipitated
  7. extractionis extracted into EtOAc (3×50 mL)
  8. washThe extracts are washed with water (2×30 mL) and brine (2×30 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78c7b5d3225e448e96513667760356eb
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…