Water → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409484Notes

Reaction equation

HRID 409484 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.[OH2:21]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:13][O:21][C:9]([CH:6]1[CH2:7][CH2:8][CH:3]([CH2:11][OH:12])[CH2:4][CH2:5]1)=[O:10].[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

8

Reactant 4

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

Product 2

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

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 h while warming to room temperature. Benzyl bromide (1.2 mL, 10 mmol) is added dropwise followed by tetrabutylammonium iodide (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 aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, (4-benzyloxymethyl-cyclohexyl)-methanol, is obtained (1.40 g, 60%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

Workup

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

Sources & evidence

ORD record
ord-e5992f3a6b994186a626a749be4310e0
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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