Lithium hydroxide, monohydrate → 1-(Carboxy)-1-(4-methoxybenzylthio)cyclopropane

HRID 22517Notes

Reaction equation

HRID 22517 reaction equation
[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][CH2:7]1)([O:3]CC)=[O:2].O.[OH-].[Li+]>C(O)C.O.O1CCCC1>[C:1]([C:6]1([S:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1)([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 224002171-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

Product 1

HCID 224002161-(Carboxy)-1-(4-methoxybenzylthio)cyclopropaneYield 96.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (0.310 g, 1.16 mmol) in 95% ethanol (6 mL), water (3 mL), and tetrahydrofuran (6 mL). Treat with lithium hydroxide monohydrate (420 mg, 10 mmol). Stir at a gentle reflux for 6 hours and evaporate the solvent in vacuo. Add water (50 mL) and wash with ether (50 mL). Acidify the aqueous phase and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopropane as a pale yellow solid (266 mg).

Workup

  1. temperaturea gentle reflux for 6 hours
  2. customevaporate the solvent in vacuo
  3. washAdd water (50 mL) and wash with ether (50 mL)
  4. extractionextract into methylene chloride (50 mL)
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-912f4d8a34614dd5adb3cbdaf203a796
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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