Benzoic Acid → Isobutyl benzoate

HRID 1283765Notes

Reaction equation

HRID 1283765 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](OC(ON=C(C#N)C(OCC)=O)=O)[CH:11]([CH3:13])[CH3:12].C(N(CC)CC)C.C(OCC)(=O)C>O>[C:1]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54067442HCID 54067442, compound

Product 1

HCID 61048Isobutyl benzoateYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising benzoic acid (1.22 g), ethyl 2-isobutoxycarbonyloxyimino-2-cyanoacetate (2.42 g), triethylamine (1.4 ml) and ethyl acetate (20 ml) is stirred at room temperature for 1 hour and then admixed with water. The ethyl acetate layer is separated and treated as in Example A to give isobutyl benzoate (1.7 g) as an oil.

Workup

  1. customThe ethyl acetate layer is separated
  2. additiontreated as in Example A

Sources & evidence

ORD record
ord-3c2b7f78dc1a4669bd165f656cf504b5
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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