Ethanol → Ethyl 3-benzoylbenzoate

HRID 1254241Notes

Reaction equation

HRID 1254241 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:23](O)[CH3:24]>>[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH2:23][CH3:24])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1013863-Benzoylbenzoic acid

Product 1

HCID 14789261Ethyl 3-benzoylbenzoate

Conditions

Temperature
100 °C

Procedure

A 100-mL round bottom flask was charged with of 3-benzoylbenzoic acid (2.20 g, 9.7 mmol), ethanol (40 mL), and sulfuric acid (3 mL). The reaction mixture was heated at 100° C. for 15 h, poured into ice water and extracted twice with Et2O. The combined organic phase was washed with satd aq NaHCO3 and dried over K2CO3. The crude ethyl 3-benzoylbenzoate was used in the next step without further purification. LC-MS (3 min) tR=1.87 min in 3 min chromatography, m/z 255 (MH+). 1H NMR (400 MHz, CDCl3) δ 8.45-8.44 (m, 1H), 8.28-8.25 (m, 1H), 8.00-7.97 (m, 1H), 7.82-7.79 (m, 2H), 7.64-7.48 (m, 4H), 4.40 (q, J=7.1 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted twice with Et2O
  2. washThe combined organic phase was washed with satd aq NaHCO3
  3. dry with materialdried over K2CO3
  4. customThe crude ethyl 3-benzoylbenzoate was used in the next step without further purification

Sources & evidence

ORD record
ord-00536539583a483481ba6bd54e701f4a
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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