p-Toluenesulfonic acid monohydrate → HCID 14566727, compound

HRID 2271039Notes

Reaction equation

HRID 2271039 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10](O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(O)(C1C=CC(C)=CC=1)(=O)=O.O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 183300457-Nitro-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 14566727HCID 14566727, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-nitro-1,2,3,4-tetrahydo-2-naphthalenol (10.13 g, 0.053 mol) (from Preparation 1) was heated in the presence of TsOH—H2O (1.72 g, 0.009 mol, 0.2 equiv.) in toluene (150 ml) for 2 h at 100° C. The solvent was removed under reduced pressure and the residue was treated with EtOAc (150 ml) and saturated aqueous NaHCO3 (150 ml). The aqueous layer was separated and extracted with additional EtOAc (2×100 ml). The combined organic layers were washed with saturated aqueous NaCl (200 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure to give 7-nitro-3,4-dihydronaphthalene as a brown oil (9.18 g, 100%) which was used in the next step without additional purification. Rf (silica gel): 0.79 (70% hexane: 30% EtOAc); 1H NMR (300 MHZ, CDCl3) 7.95 (dd, J=2.4 and 8.1 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 7.21 (d, J=8.1 Hz, 1H), 6.50 (d, J=6.50 Hz, 1H), 6.18 (dt, J=4.5 and 9.6 Hz, 2H), 2.88 (t, J=8.4 Hz, 2H), 2.40-2.34 (m, 2H); 13C NMR (75 MHZ, CDCl3) 147.1, 143.1, 135.3, 131.4, 128.2, 126.5, 121.8, 120.3, 27.4, 22.5.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with EtOAc (150 ml) and saturated aqueous NaHCO3 (150 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with additional EtOAc (2×100 ml)
  5. washThe combined organic layers were washed with saturated aqueous NaCl (200 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21b3215ea7714b54a7725a8fb0096a79
Source dataset
uspto-grants-2001_12
Patent number
US06333337B1

Reaction notes

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