Methanol → Methyl 4-benzoylbutyrate

HRID 498141Notes

Reaction equation

HRID 498141 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].OS(O)(=O)=O.O.[CH3:21]O>>[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:21])=[O:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 73914delta-Oxobenzenepentanoic acid

Product 1

HCID 137042Methyl 4-benzoylbutyrate

Procedure

A solution of 50.0 g of 5-oxo-5-phenylpentanoic acid (260 mmol) (origin: Fluka) and 70 ml of conc. H2SO4 in 1400 ml of methanol was heated under reflux for 1 h. The reaction mixture was cooled down to room temperature and added to 2 l of water and extracted with ether (2×). The organic phase was washed with water (1×), an aq. solution of NaHCO3 (10%, 2×), again with water (2×), dried (Na2SO4) and concentrated to give 47.9 g (90%) of a slightly yellow oil, which slowly crystallizes at 4° C.

Workup

  1. temperatureunder reflux for 1 h
  2. extractionextracted with ether (2×)
  3. washThe organic phase was washed with water (1×)
  4. dry with materialan aq. solution of NaHCO3 (10%, 2×), again with water (2×), dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give 47.9 g (90%) of a slightly yellow oil, which
  7. customslowly crystallizes at 4° C.

Sources & evidence

ORD record
ord-0e8473d369bf422191daaeb90a7e8972
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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