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

HRID 5876Notes

Reaction equation

HRID 5876 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[C:5]2[O:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]3[C:4]=2[CH:3]=1>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:5]2[O:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]3[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 14621140Methyl 2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Product 1

HCID 146211442-Chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.6 g of methyl 2-chloro-5a,6,7, 8,9,9a-hexahydrodibenzofuran-4-carboxylate in 10 ml of methanol and 20 ml of 1N sodium hydroxide is stirred at 50° C. for 6 hours. This is cooled, the methanol is removed under vacuo, diluted with 30 ml water and filtered. The aqueous solution is acidified with acetic acid, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated to dryness to give crystalline product which is used directly in the next step.

Workup

  1. temperatureThis is cooled
  2. customthe methanol is removed under vacuo
  3. additiondiluted with 30 ml water
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness
  9. customto give crystalline product which

Sources & evidence

ORD record
ord-4563d094e20d4ff7b79cc94364998fa9
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Reaction notes

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