HCID 54330519, compound → Methyl 2-chloro-trans-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

HRID 1032844Notes

Reaction equation

HRID 1032844 reaction equation
[CH2:1]([C:7]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]=1[OH:18])[CH2:2][CH:3]=[CH:4][CH2:5][CH3:6]>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 54330519HCID 54330519, compound

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-hexenyl)-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% ethylacetate/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-0add7dd818414d7cad92b4757ad94146
Source dataset
uspto-grants-1990_09
Patent number
US04959485

Reaction notes

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