Methyl 3-(3-cyclohexenyl)-5-chlorosalicylate → Methyl 2-chloro-trans-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate
Reaction equation
[CH:1]1([C:7]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]=2[OH:18])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1>FC(F)(F)C(O)=O>[Cl:17][C:15]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]2[O:18][C@@H:2]3[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]3[C:7]=2[CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 9 g of methyl 3-(3-cyclohexenyl)-5-chlorosalicylate and 20 ml trifluoroacetic acid is heated at 70° C. overnight. The cooled reaction mixture is diluted with hexanes, washed three times with water, dried and evaporated to dryness. The residue is purified with flash chromatography using 10% ethyl acetate/hexane to give four fractions. First fraction 2.29 of material (mixture of at least two materials); second fraction 2.29 cis isomer; third fraction 1.69 mixture of cis and trans isomers; and fourth fraction 19 trans isomer.
Workup
- customThe cooled reaction mixture
- washwashed three times with water
- customdried
- customevaporated to dryness
- customThe residue is purified with flash chromatography
- customto give four fractions
- additionFirst fraction 2.29 of material (mixture of at least two materials)
- additionthird fraction 1.69 mixture of cis and trans isomers
Sources & evidence
- ORD record
- ord-eb0ad06e2a2146e7b18095721cf92b17
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05288731
Reaction notes
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