Potassium Carbonate → 3-Benzyl-2-cyclohepten-1-ol

HRID 2230086Notes

Reaction equation

HRID 2230086 reaction equation
[CH2:1]([C:8]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10](=[O:15])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+]>CCOCC>[CH2:1]([C:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([OH:15])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129670393-Benzyl-2-cyclohepten-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 129670403-Benzyl-2-cyclohepten-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-benzyl-2-cyclohepten-1-one (3.1 g, 18 mmol) in either 100 mL) was slowly added to a suspension of lithium aluminum hydride (LAH) (684 mg, 0.87 mol) and ether (100 mL) at 0° C. under N2. The resulting mixture was stirred overnight at ambient temperature and cooled to 0° C. Saturated K2CO3 solution was added to quench the excess LAH, the mixture was filtered through Celite and washed with several portions of ether. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give the title compound (3 g, 93%) as a colorless oil. NMR (CDCl3):3.32(ABq,J=6 Hz,2H, benzylic protons), 4.42 (bs, 1H, CHOH), 5.58 (bs, 1H, olefinic proton), 7.22 (m, 5H, aromatic protons).

Workup

  1. temperaturecooled to 0° C
  2. customto quench the excess LAH
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with several portions of ether
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61eb4b6f5a2c4e788f56c20f8111d79d
Source dataset
uspto-grants-2002_07
Patent number
US06423714B1

Reaction notes

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