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

HRID 1606911Notes

Reaction equation

HRID 1606911 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-164f0514fbfe45bf82e47f63642b75a0
Source dataset
uspto-grants-1989_09
Patent number
US04863921

Reaction notes

Loading…