Hydrochloric Acid → 4-(3-Oxobutyl)benzoic acid

HRID 736496Notes

Reaction equation

HRID 736496 reaction equation
[C:1]([CH2:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].C[O-].[Na+].C[O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18]C(CBr)=[CH:16][CH:15]=1.Cl>CC(O)=O>[O:3]=[C:1]([CH3:2])[CH2:4][CH2:5][C:6]1[CH:18]=[CH:19][C:14]([C:13]([OH:22])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 31261AcetylacetoneHCID 256687Methyl 4-(bromomethyl)benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 145792564-(3-Oxobutyl)benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of acetyl acetone (5.0 ml, 49 mmol) at room temperature NaOMe (25% wt, 10.8 ml, 47.3 mmol) was added followed by 4-bromomethyl-benzoic acid methyl ester 2 (9.0 g, 39.3 mmol). The reaction mixture refluxed 3 hours, cooled to the room temperature and acidified with HCl (pH 1-2). Evaporation of the resultant solution yielded a residue, which was refluxed in a mixture of glacial AcOH (50 ml) and conc. HCl (25 ml) for 4 hours. Acids were removed in vacuum and the residue was triturated with water to form a crystalline material, which was collected by filtration and dried to afford 278 (6.72 g, 80% yield). [M−1] 191.1.

Workup

  1. temperatureThe reaction mixture refluxed 3 hours
  2. customEvaporation of the resultant solution
  3. customyielded a residue, which
  4. customAcids were removed in vacuum
  5. customthe residue was triturated with water
  6. customto form a crystalline material, which
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f41458ce9952412db0a775c1e4b79440
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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