Water → HCID 57050621, compound

HRID 1292631Notes

Reaction equation

HRID 1292631 reaction equation
[OH:1][CH2:2][CH:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([CH3:11])[CH2:7][C@H:6]1[OH:12])[CH3:4].[H-].[Na+].[CH:15](I)([CH3:17])[CH3:16].O>C(COC)OC>[CH:15]([O:1][CH2:2][CH:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([CH3:11])[CH2:7][C@H:6]1[OH:12])[CH3:4])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 11062881HCID 11062881, compound

Product 1

HCID 57050621HCID 57050621, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

20.0 g (0.12 mol) of (1R, 2S, 5R)-2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanol was dissolved in 100 ml of dimethoxyethane, and 3.3 g (0.14 mol) of sodium hydride was added to the solution. The mixture was agitated for 30 min, and 23.7 g (0.14 mol) of isopropyl iodide was dropped thereinto and continued to agitate at room temperature for 24 hr. After the completion of the reaction, 300 ml of water was added to the reaction fluid and agitated. The reaction product was extracted with ether. The resultant ether phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off, thereby obtaining 18.3 g (yield: 73.6%) of (1R, 2S, 5R)-2-(2-isopropoxy-1-methylethyl)-5-methylcyclohexanol in the form of a colorless liquid. The mass spectrometry and NMR data of the obtained compound are as follows:

Workup

  1. stirringto agitate at room temperature for 24 hr
  2. additionwas added to the reaction fluid
  3. stirringagitated
  4. extractionThe reaction product was extracted with ether
  5. dry with materialThe resultant ether phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3974f678d5504acda75bd0070bfed7fa
Source dataset
uspto-grants-1998_05
Patent number
US05756857

Reaction notes

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