p-Toluenesulfonic acid → HCID 54446076, compound

HRID 486582Notes

Reaction equation

HRID 486582 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:14][CH:15](O)[CH:16]=[CH2:17].COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:14]([CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[CH:15]=[CH:16][CH3:17]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane2×HCID 117163-Buten-2-ol2×HCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 54446076HCID 54446076, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-dihydro-6-methoxy-1(2H)-naphthalenone (198 g) was dissolved in 2000 ml of toluene under argon and treated in succession with 193 ml of 3-buten-2-ol, 206 ml of 2,2-dimethoxypropane and 1.9 g of p-toluenesulphonic acid. The reaction mixture was boiled at reflux for 20 hours, treated with a further 175 ml of 3-buten-2-ol and 180 ml of 2,2-dimethoxypropane and boiled for a further 50 hours. After cooling the solution was washed with 500 ml of saturated sodium hydrogen carbonate solution, the aqueous phase was extracted once with 600 ml of ethyl acetate, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 269 g of brown oil, was chromatographed on 3000 g of silica gel with hexane/diethyl ether (5:1) as the eluent. There were obtained 147 g (57%) of 2-(2-butenyl)-3,4-dihydro-6-methoxy-1(2H)-naphthalenone which was processed without further purification.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureAfter cooling the solution
  3. washwas washed with 500 ml of saturated sodium hydrogen carbonate solution
  4. extractionthe aqueous phase was extracted once with 600 ml of ethyl acetate
  5. dry with materialdried with MgSO4
  6. customThe residue, 269 g of brown oil, was chromatographed on 3000 g of silica gel with hexane/diethyl ether (5:1) as the eluent

Sources & evidence

ORD record
ord-ae115a13033d4089b34244009491a93b
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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