p-Toluenesulfonic acid → HCID 12419583, compound

HRID 974177Notes

Reaction equation

HRID 974177 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH2:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 12419583HCID 12419583, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

4 g of 7-nitro-1,2,3,4-tetrahydro-1-naphthalenol [J. Pharm. Soc. Japan, Vol. 64, (1944), p. 153], 53 ml of toluene and 180 mg of p-toluene sulfonic acid were mixed together and then stirred for 2 hours at 130° C. while distilling off ≃20 ml of solvent. Then, at 20° C. 50 ml of water were added and extraction was done with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium bicarbonate, and with a saturated aqueous solution of sodium chloride, dried and concentrated to dryness. The residue was crystallized from ethanol to obtain 2.75 g of the expected product melting at ≃35° C. and after crystallizing from isopropanol melting at 37° C.

Workup

  1. distillationwhile distilling off ≃20 ml of solvent
  2. customat 20° C
  3. addition50 ml of water were added
  4. extractionextraction
  5. washThe extracts were washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialwith a saturated aqueous solution of sodium chloride, dried
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-d86297cb9ec34cdc9de426149b7af4c3
Source dataset
uspto-grants-1991_11
Patent number
US05068244

Reaction notes

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