Water → ((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

HRID 2091988Notes

Reaction equation

HRID 2091988 reaction equation
[H-].[Na+].[C@H:3]1([CH2:11][OH:12])[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:13]([O:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([CH2:11][OH:12])[CH2:4][CH2:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178520956HCID 178520956, compound

Product 1

HCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanolYield 60%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaH (440 mg, 11 mmol) in THF (22 mL) is added trans-1,4-cyclohexanedimethanol (1.44 g, 10 mmol) at 0° C., and the mixture is stirred for 1 hour while warming to room temperature. Benzyl bromide (1.2 mL, 10 mmol) is added dropwise followed by TBAI (185 mg, 0.5 mmol). The reaction is heated to 60° C. for 15 hours. After cooling to room temperature, H2O is added, and the mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain (4-benzyloxymethyl-cyclohexyl)-methanol as clear oil (1.40 g, 60%) after purification.

Workup

  1. temperatureThe reaction is heated to 60° C. for 15 hours
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture is extracted with EtOAc
  4. dry with materialThe combined organic layer after dried over MgSO4
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-fe20796803a64a1b9948759a84b0c6b1
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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