Acetone → 3-(3-Oxo-butyryl)-benzoic acid methyl ester

HRID 1725517Notes

Reaction equation

HRID 1725517 reaction equation
[C:1]([O:13]C)(=O)[C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1.[CH3:15][C:16]([CH3:18])=[O:17].[H-].[Na+].Cl>C1(C)C=CC=CC=1.O>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([C:1](=[O:13])[CH2:15][C:16](=[O:17])[CH3:18])[CH:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 15088Dimethyl isophthalateHCID 24758Sodium hydride

Product 1

HCID 205039193-(3-Oxo-butyryl)-benzoic acid methyl esterYield 13.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of dimethyl isophthalate (12 g, 61.85 mmole) and acetone (5 mL, 68 mmole) in a mixture of toluene/dimethoyethane (90 mL/30 mL) was added to a suspension of NaH 60% (2.97 g, 74.23 mmole) in dry toluene (30 mL) under argon. The mixture was heated at 100° C. for 4 hours. The reaction mixture was cooled to rt and 25 mL of water were added. The mixture was poured into water (250 mL) and the pH was adjusted to 3-4 with HCl 2N. The aqueous mixture was extracted with ethyl acetate (2×250 mL), washed with brine, dried over sodium sulphate and evaporated to afford a yellow solid which was purified by column cromatography (n-Hex/EtOAc 9:1 to 8:2) to afford the title compound (1.78 g, 11% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe aqueous mixture was extracted with ethyl acetate (2×250 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto afford a yellow solid which
  7. customwas purified by column cromatography (n-Hex/EtOAc 9:1 to 8:2)

Sources & evidence

ORD record
ord-89305eeb65204e3a86130e63fcd5518c
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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