1-Propanol → Propyl 4-benzoylbenzoate

HRID 1679252Notes

Reaction equation

HRID 1679252 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(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:28](O)[CH2:29][CH3:30]>>[CH2:28]([O:14][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH2:29][CH3:30]

Participants

5

Reactant 4

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 691474-Benzoylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 53832472Propyl 4-benzoylbenzoateYield 76.3%

Procedure

A mixture of 10.0 grams (0.044 mole) of p-benzoylbenzoic acid, 100 milliliters of n-propanol and 0.25 milliliters of concentrated sulfuric acid was stirred under reflux for 5 hours. Aqueous sodium bicarbonate solution was then added. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. Volatiles were removed under vacuum with warming to provide 9.0 grams (76.3% yield) of n-propyl-p-benzoylbenzoate. The infrared spectrum revealed carbonyl absorption bands at 1670 and 1730 cm-1.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customVolatiles were removed under vacuum
  6. temperaturewith warming

Sources & evidence

ORD record
ord-e62801858c1c4175acca1ad7d7c2b9b4
Source dataset
uspto-grants-1978_03
Patent number
US04080275

Reaction notes

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