Triethanolamine → Ethyl 6-hydroxy-4-methylhexa-2,4-dienoate
Reaction equation
C([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].N(CCO)(CCO)CCO.C(OCC)(=O)C>C(O)C>[OH:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
27.5 g of ethyl 6-acetoxy-4-methyl-2,4-hexadienoate, 20 g of sodium carbonate and 2 ml of triethanolamine were heated to reflux for 3 hours in 250 ml of ethanol. After the addition of ethyl acetate, the organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Distillation at 110° C./0.4 mmHg gave 15.7 g (71%) of ethyl 6-hydroxy-4-methyl-2,4-hexadienoate.
Workup
- washthe organic phase was washed with saturated sodium chloride solution
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- distillationDistillation at 110° C./0.4 mmHg
Sources & evidence
- ORD record
- ord-ea7b9da8a510461684ede7de40d5d547
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539154
Reaction notes
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