Hydrochloric Acid → HCID 22591689, compound

HRID 1784491Notes

Reaction equation

HRID 1784491 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]23[CH2:17][CH2:16][C:13]([C:18]([O:20]C)=[O:19])([CH2:14][CH2:15]2)[CH2:12][CH2:11]3)[O:6][CH2:5][CH2:4][O:3]1.CO.[OH-].[K+].Cl>O>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]23[CH2:11][CH2:12][C:13]([C:18]([OH:20])=[O:19])([CH2:16][CH2:17]2)[CH2:14][CH2:15]3)[O:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 22591683HCID 22591683, compound

Product 1

HCID 22591689HCID 22591689, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]octane-1-carboxylate (4-C) (1.0 g, 3.38 mmol) was stirred in a solution of 90% methanol and 10% water (50 mL). Excess potassium hydroxide (2.0 g) was added. The mixture was refluxed overnight. The cooled mixture was acidified with 1N hydrochloric acid (100 mL) and then washed twice with ethyl acetate (100 mL). The combined organic layers were dried (MgSO4). Ethyl acetate was removed in vacuo yielding pure 4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid (4-D).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. washwashed twice with ethyl acetate (100 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customEthyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-459c5cfb913d41c4829308c412ec545b
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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