Hydrogen Peroxide → Methyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate

HRID 2225498Notes

Reaction equation

HRID 2225498 reaction equation
CSC.B.[CH3:5][C:6]1([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:10][C:9](=[CH2:12])[CH2:8][CH2:7]1.[H][H].[OH-:19].[Na+].OO.[Cl-].[Na+]>C1COCC1.O>[OH:19][CH2:12][CH:9]1[CH2:8][CH2:7][C:6]([CH3:5])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:10]1

Participants

9

Reactant 6

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19004635Methyl 1-methyl-4-methylidenecyclohexane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19004700Methyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon stream, 12 ml of borane-dimethy sulfide complex (THF 2M solution) was added to a solution of 7 g of methyl 1-methyl-4-methylene-1-cyclohexanecarboxylate (Example 41) in 200 ml of THF, under ice-cooling. The resultant solution was reacted for 2.5 hours at room temperature. Then, 100 ml of purified water was added to the reaction solution. After hydrogen gas ceases to be generated, 50 ml of 3N aqueous sodium hydroxide solution was added to the solution under ice-cooling. Ten minutes later, 50 ml of an aqueous hydrogen peroxide solution was added, and the resultant solution was stirred for 1 hour at 50° C. After reaction, 500 ml of an aqueous sodium chloride solution was added to the reaction solution, thereby isolating the THF layer, which was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 4.5 g of methyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate as a colorless oil, which had the following physiochemical properties:

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionwas added to the reaction solution
  4. dry with materialwas dried over magnesium sulfate
  5. customThereafter, the solvent was removed in vacuo
  6. customThe oily substance obtained
  7. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9a9afc6ab9794f0dadebb661b8d58e76
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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