2-Tetralone → Naphthalene, 1,2-dihydro-3-methoxy-

HRID 2211371Notes

Reaction equation

HRID 2211371 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[CH:12]([O-])([O-])OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:12][O:11][C:2]1[CH2:3][CH2:4][C:5]2[C:10]([CH:1]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 682662-TetraloneHCID 521998p-Toluenesulfonic acid monohydrateHCID 53629101Methylorthoformate

Product 1

HCID 11105653Naphthalene, 1,2-dihydro-3-methoxy-Yield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.4 g of 2-tetralone, 1.5 mL of methyl orthoformate, and a few crystals of para-toluenesulfonic acid monohydrate in 75 mL of benzene was stirred for 22 hours and then evaporated in vacuo. The residue was chromatographed on Florisil® eluting with hexane/ethyl ether to provide 1.15 g (75%) of the desired title intermediate. NMR.

Workup

  1. customevaporated in vacuo
  2. customThe residue was chromatographed on Florisil®
  3. washeluting with hexane/ethyl ether

Sources & evidence

ORD record
ord-e82e2fce827e40b7ad8e30cea3f679d0
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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