Reaction equation
[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1.[C:13]([O:18]C(=O)C(C)C)(=[O:17])[CH:14]([CH3:16])[CH3:15]>>[C:13]([OH:18])(=[O:17])[CH:14]([CH3:16])[CH3:15].[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
166 g of ethylvanillin are introduced into a 500 ml three-neck flask fitted with a 30 cm packed column and melted, and 189.6 g of isobutyric anhydride are added at a maximum temperature of 100° C. The reaction is only slightly exothermic. When addition is complete, the isobutyric acid can firstly be distilled off at a still temperature of 120° C. and 150 mbar, and iso-butyric acid and excess anhydride can finally be distilled at up to 130° C. and 20 mbar. The system is allowed to cool to 90° C., 500 ml of isopropanol are added and crystallization takes place upon further stirring and cooling to 7° C. The crystals are filtered off with suction, washed twice with 60 ml of cold isopropanol and dried, giving 182 g of ethylvanillin isobutyrate. Repeated crystallization from the mother liquor produces another 22.8 g of ethylvanillin isobutyrate.
Workup
- customfitted with a 30 cm
- additionWhen addition
- distillationthe isobutyric acid can firstly be distilled off at a still temperature of 120° C. and 150 mbar, and iso-butyric acid and excess anhydride
- distillationcan finally be distilled at up to 130° C.
- addition500 ml of isopropanol are added
- customcrystallization
- temperaturecooling to 7° C
- filtrationThe crystals are filtered off with suction
- washwashed twice with 60 ml of cold isopropanol
- customdried
Sources & evidence
- ORD record
- ord-12788f8f528040179f9510eaeb12b99c
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874398
Linked notes
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