Isobutyric Acid → 3-Methylbenzyl isobutyrate

HRID 1869123Notes

Reaction equation

HRID 1869123 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-b1a6c86573a54277af7d910392b171e0
Source dataset
uspto-grants-2009_12
Patent number
US07638479B2

Reaction notes

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