Methanol → Methyl 4-benzoylbenzoate

HRID 2241037Notes

Reaction equation

HRID 2241037 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:22]O>>[C:2]1([C:1]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:22])=[O:14])=[CH:16][CH:17]=2)=[O:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 691474-Benzoylbenzoic acid

Product 1

HCID 349620Methyl 4-benzoylbenzoateYield 64%

Procedure

A stirring solution of MeOH, 4-benzoylbenzoic acid and thionyl chloride was refluxed for 7 h under a nitrogen atmosphere. The reaction was cooled to RT and a white solid precipitated. The mixture was refrigerated overnight then filtered, rinsed with ice chilled MeOH and air-dried to yield 6.10 g (64%) of the title compound 19 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ8.09 (d, J=8.2 Hz, 2H), 7.85 (d, J=8.1 Hz, 2H), 7.54-7.74 (m, 5H), 3.88 (s, 3H).

Workup

  1. customa white solid precipitated
  2. filtrationthen filtered
  3. washrinsed with ice
  4. temperaturechilled MeOH
  5. customair-dried

Sources & evidence

ORD record
ord-ad3676d848574f7493144fdfd8f8b7d9
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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