Acetone → 2-Methoxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-one

HRID 6735Notes

Reaction equation

HRID 6735 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][C:11](OC)([O:13]C)[CH2:10][CH2:9][CH2:8][C:7]=2[CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>O.ClCCl.C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:17]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 123538292,6,6-trimethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene

Product 1

HCID 123691772-Methoxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-oneYield 80.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2,6,6-trimethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene (387 mg) and p-toluenesulfonic acid monohydrate (31 mg) was stirred in 5 mL of 1:1 water:acetone. The mixture was diluted with 50 mL of dichloromethane and 50 mL of saturated sodium hydrogen carbonate. The aqueous layer was re-extracted with 50 mL more dichloromethane and the combined organics were dried over sodium sulfate. Evaporation of the solvent gave 250 mg of 2-methoxy-5,7,8,9-tetrahydro-benzocyclohepten-6-one, which was converted to 2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamine by using Procedure X.

Workup

  1. extractionThe aqueous layer was re-extracted with 50 mL more dichloromethane
  2. dry with materialthe combined organics were dried over sodium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-443e59999fd64eac976cc8d305d90497
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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