HCID 57577327, compound → 4-[(Tetrahydro-3-furanyl)oxy]cyclohexanol

HRID 420769Notes

Reaction equation

HRID 420769 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:2]1>[OH-].[Na+].[Rh]>[O:1]1[CH2:5][CH2:4][CH:3]([O:6][CH:7]2[CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12]2)[CH2:2]1

Participants

4

Reactant 1

HCID 57577327HCID 57577327, compound

Product 1

HCID 575773334-[(Tetrahydro-3-furanyl)oxy]cyclohexanolYield 86%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

4-(Tetrahydro-furan-3-yloxy)-phenol (900 mg, 5.00 mmol) was dissolved in 25 ml 0.4N NaOH and stirred with 500 mg Rh/C 5% under hydrogen atmosphere at 60° C. and 4 bar pressure for 3 hours. The catalyst was filtered off and the clear solution acidified with conc. H2SO4 to pH 1. The aqueous layer was saturated with NaCl and extracted two times with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product (800 mg, 86%) was obtained as a light brown liquid and used without any further purification for the next step.

Workup

  1. filtrationThe catalyst was filtered off
  2. extractionextracted two times with dichloromethane
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-757c8d964e4245458d6af5ce3b8e668f
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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