Methyl 3-(3-cyclohexenyl)-5-chlorosalicylate → Methyl 2-chloro-trans-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

HRID 5889Notes

Reaction equation

HRID 5889 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]=1

Participants

3

Reactant 1

HCID 15171280Methyl 3-(3-cyclohexenyl)-5-chlorosalicylate

Product 1

HCID 14621143Methyl 2-chloro-trans-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 9 g of methyl 3-(3-cyclohexenyl)-5chlorosalicylate 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

Workup

  1. customThe cooled reaction mixture
  2. washwashed three times with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue is purified with flash chromatography
  6. customto give four fractions

Sources & evidence

ORD record
ord-624b3fc71b5241e7a87be65e3b8537a0
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Reaction notes

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