Hydrochloric Acid → HCID 21502429, compound

HRID 1288528Notes

Reaction equation

HRID 1288528 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:14]([O:16]C)=[O:15])[CH2:9]1.[OH-].[Na+].Cl>C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:14]([OH:16])=[O:15])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21502425HCID 21502425, compound

Product 1

HCID 21502429HCID 21502429, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g. of methyl 3-[(tetrahydropran-2-yl)oxy]-bicyclo[3.1.0]hexane-6-carboxylate (VIII, syn and anti, from Example 3), ethanol (45 ml.), and sodium hydroxide (10 ml. of a 20% aqueous solution) is refluxed for 20 minutes. Cooling evaporation of the ethanol under reduced pressure, and addition of 100 ml. of water gives a solution which is acidified with dilute hydrochloric acid and extracted with diethyl ether. The diethyl ether extract is dried with anhydrous sodium sulfate and evaporated to give a mixture of exo syn and anti 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylic acid.

Workup

  1. additionA mixture of 5 g
  2. temperatureCooling
  3. customevaporation of the ethanol
  4. additionunder reduced pressure, and addition of 100 ml
  5. customof water gives a solution which
  6. extractionextracted with diethyl ether
  7. extractionThe diethyl ether extract
  8. dry with materialis dried with anhydrous sodium sulfate
  9. customevaporated
  10. customto give

Sources & evidence

ORD record
ord-06c2e2f0a74544e1811e3935191d4954
Source dataset
uspto-grants-1976_10
Patent number
US03988372

Reaction notes

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