Ethanol → 1-(Carboxy)-1-(4-methoxybenzylthio)cyclohexane

HRID 260694Notes

Reaction equation

HRID 260694 reaction equation
[C:1]([C:6]1([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)([O:3]CC)=[O:2].[OH-].[Na+].C(O)C.O.[OH-].[Li+]>O.O1CCCC1>[C:1]([C:6]1([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 224002131-(Carboethoxy)-1-(4-methoxybenzylthio)cyclohexane

Product 1

HCID 212169071-(Carboxy)-1-(4-methoxybenzylthio)cyclohexaneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclohexane (1.45 g, 4.7mmol) in water (2.5 mL) and tetrahydrofuran (10 mL). Treat with 2.5N sodium hydroxide (4 mL, 10mmol. Heat at 60° C. for 2 hours, add 95% ethanol (10 mL) and lithium hydroxide monohydrate (0.42 g, 10 mmol) Heat to a gentle reflux for 20 hours, cool and evaporate the solvent in vacuo. Partition between water (50 mL) and ether (50 mL). Separate the aqueous phase and acidify to pH 1. Extract with methylene chloride (50 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclohexane as a white solid (1.21 g, 92%).

Workup

  1. temperatureHeat to
  2. temperaturea gentle reflux for 20 hours
  3. temperaturecool
  4. customevaporate the solvent in vacuo
  5. customPartition between water (50 mL) and ether (50 mL)
  6. customSeparate the aqueous phase
  7. extractionExtract with methylene chloride (50 mL)
  8. dry with materialdry (Na2SO4)
  9. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-8ffcce36864f4fd889b31a46a3758e78
Source dataset
uspto-grants-1996_06
Patent number
US05529996

Reaction notes

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