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

HRID 217236Notes

Reaction equation

HRID 217236 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-ba6535fc556644678cb7ac7c0f4a84b8
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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