Sulfuric Acid → 3-Benzyl-2-cyclohepten-1-one

HRID 2230085Notes

Reaction equation

HRID 2230085 reaction equation
C(O[C:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH:5]=1)C.[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.OS(O)(=O)=O>C1COCC1>[CH2:12]([C:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH:5]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 156706513-Ethoxycyclohept-2-en-1-oneHCID 178418336HCID 178418336, compound

Product 1

HCID 129670393-Benzyl-2-cyclohepten-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-ethoxy-2-cyclohepten-1-one(5 g, 0.89 mol) in THF (70 mL) was added at room temperature to a solution of 2M benzyl magnesium chloride (800 ml) under N2 and stirred for 6 h. The resulting mixture was poured into a solution of 30% H2SO4 and stirred for 5 h. The resulting organic layer was separated, and the aqueous layer was extracted with several portions of ether. The combined organic layer was dried (MgSO4), and concentrated in vacuo to give 3-benzyl-2-cyclohepten-1-one (3.1 g, 65%) as a colorless oil. NMR (CDCl3); 3.45(s,2H1benzylic protons), 5.97 (bs, 1H, olefinic proton), 7.22 (m, 5H, aromatic protons).

Workup

  1. stirringstirred for 5 h
  2. customThe resulting organic layer was separated
  3. extractionthe aqueous layer was extracted with several portions of ether
  4. dry with materialThe combined organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f53ffc802a5847ee9bd75e756d2b4855
Source dataset
uspto-grants-2002_07
Patent number
US06423714B1

Reaction notes

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