Cycloheptanecarboxylic acid → Cycloheptanemethanol

HRID 1018844Notes

Reaction equation

HRID 1018844 reaction equation
O1CCCC1.B.[CH:7]1([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[CH:7]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 15091Cycloheptanecarboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 78193CycloheptanemethanolYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of borane tetrahydrofuran complex (95 mL of 1.5 M solution in tetrahydrofuran/ether) under argon at 0° C. was added cycloheptanecarboxylic acid (10.05 g; 69.3 mmol) in 30 mL tetrahydrofuran. After 2 h, the mixture was quenched by careful addition of methanol and the mixture concentrated in vacuo. The residue was taken up into ethyl acetate and washed with successively with 1N HCl, saturated sodium bicarbonate and brine solutions. The organic layer was dried (sodium sulfate) filtered and concentrated in vacuo to give 9.19 g (100%) of cycloheptane methanol as a colorless oil.

Workup

  1. customthe mixture was quenched by careful addition of methanol
  2. concentrationthe mixture concentrated in vacuo
  3. washwashed with successively with 1N HCl, saturated sodium bicarbonate and brine solutions
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f85108cc48e54384a5a91a8948bea87e
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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