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

HRID 22519Notes

Reaction equation

HRID 22519 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)cyclohexane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclohexane (1.45 g, 4.7 mmol) in water (2.5 mL) and tetrahydrofuran (10 mL). Treat with 2.5N sodium hydroxide (4 mL, 10 mmol). 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 (l.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-e57f3bdf09de44f283081084229aa7b8
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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