Methyl 2-chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate → 2-Chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

HRID 1606912Notes

Reaction equation

HRID 1606912 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[C:5]2[O:6][C@@H:7]3[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]3[C:4]=2[CH:3]=1>[OH-].[Na+].O1CCOCC1.O>[Cl:1][C:2]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:5]2[O:6][C@@H:7]3[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]3[C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 14621142Methyl 2-chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Product 1

HCID 146211462-Chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2 g methyl 2-chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate in 30 ml 1N sodium hydroxide and 5 ml dioxane is stirred at 60° C. for 5 hours. This is then diluted with water, filtered, acidified with acetic acid, extracted with ethyl acetate, dried over magnesium sulfate and evaporated to dryness to obtain an oily product which crystallizes on standing. This is recrystallyzed to obtain 2-chloro-cis-5a,6,7,8,9,9a-hexahydrodibenzo-furan-4-carboxylic acid. (M.P. 132°-134° C.)

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customto obtain an oily product which
  6. customcrystallizes

Sources & evidence

ORD record
ord-fa0d3392c59c40aca1c887b1fa658599
Source dataset
uspto-grants-1989_09
Patent number
US04863921

Reaction notes

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