Hydrochloric Acid → 4-(4-Oxo-4-phenyl-butyryl)-benzoic acid

HRID 1725158Notes

Reaction equation

HRID 1725158 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[CH2:12][CH2:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)C.[OH-].[K+].Cl>C1COCC1>[O:21]=[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:23])=[O:3])=[CH:6][CH:7]=1)=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 44520324-(4-Oxo-4-phenyl-butyryl)-benzoic acid ethyl ester

Product 1

HCID 574236664-(4-Oxo-4-phenyl-butyryl)-benzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

4-(4-Oxo-4-phenyl-butyryl)-benzoic acid ethyl ester (3.22 g, 10.4 mmol) is dissolved in THF (100 mL) and an aqueous solution of KOH (15.6 mmol in 50 mL) is added. The reaction is stirred and heated (65° C.) for 6 h, whereupon HPLC analysis indicated the formation of a single product at the expense of the diketone. The reaction is neutralized with aqueous HCl and the THF removed in vacuo. The resulting solid is dissolved in EtOAc and the organic phase dried (Na2SO4), filtered and concentrated to afford 2.93 g (>99%) of the desired carboxylic acid (RT=0.90). LCMS confirmed the identity of the product (ES+Exact Mass: 282.09, Obs.: 283.48). This product is used without further purification.

Workup

  1. customthe THF removed in vacuo
  2. dissolutionThe resulting solid is dissolved in EtOAc
  3. dry with materialthe organic phase dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e6484ba8d164384850040eca40f606d
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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