Isobutyric Acid → 3-Methylbenzyl isobutyrate

HRID 1726845Notes

Reaction equation

HRID 1726845 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10](O)(=[O:14])[CH:11]([CH3:13])[CH3:12]>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:10]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=1)(=[O:14])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 6590Isobutyric AcidHCID 114763-Methylbenzyl alcohol

Product 1

HCID 575649983-Methylbenzyl isobutyrateYield 60%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent2×

Procedure

25 g (0.2 mol) of 3-methylbenzyl alcohol (Aldrich), 18 g (0.2 mol) of isobutyric acid and 0.6 g of p-toluenesulfonic acid are heated in a 500 ml three-necked flask apparatus with a water separator until the water is completely separated. Washing is then firstly performed with diluted sodium hydrogencarbonate solution and thereafter with water. After removing the toluene by distillation, the residue is distilled using a bulb tube distillation oven. 23 g of product (60% of theoretical) is obtained.

Workup

  1. customis completely separated
  2. washWashing
  3. customAfter removing the toluene
  4. distillationby distillation
  5. distillationthe residue is distilled
  6. distillationdistillation oven

Sources & evidence

ORD record
ord-11e49ae0bd1e4694a31d3098a2ab5dd9
Source dataset
uspto-grants-2009_02
Patent number
US07494967B2

Reaction notes

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