Trifluoroacetic acid → 4-Methyl-3-formyl-pent-3-en-1-oic acid
Reaction equation
[CH3:1][C:2]([CH3:14])=[C:3]([CH:12]=[O:13])[CH2:4][C:5]([O:7]C(C)(C)C)=[O:6].FC(F)(F)C(O)=O.C1CCCCC1>C(Cl)Cl>[CH3:1][C:2]([CH3:14])=[C:3]([CH:12]=[O:13])[CH2:4][C:5]([OH:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of 0.956 g of tert.-butyl 4-methyl-3-formyl-pent-3-enoate in 8.7 ml of methylene chloride was added at 0° to 5° C. to a mixture of 15.5 ml of trifluoroacetic acid and 20 ml of methylene chloride and the mixture was stirred at 5° C. for 3 hours. Cyclohexane was added to the mixture which was then evaporated to dryness under reduced pressure. The residue was empasted with isopropyl ether to obtain 0.444 g of 4-methyl-3-formyl-pent-3-en-1-oic acid melting at 102° C. The mother liquors were chromatographed over silica gel and elution with a 1-1-1 benzene-acetone-chloroform mixture yielded 40 mg of 4-methyl-3-formyl-pent-3-en-1-oic acid melting at 102° C.
Workup
- customwas then evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-b647ddc2da904aaa86525a50bfa3111a
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04487957
Reaction notes
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