Potassium Nitrate → 5'-Nitro-spiro(cyclopentane-1,1'-indan)-3'-one

HRID 426912Notes

Reaction equation

HRID 426912 reaction equation
[C:1]12([CH2:14][CH2:13][CH2:12][CH2:11]1)[C:9]1[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:3](=[O:10])[CH2:2]2.[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O>[N+:15]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[C:1]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:2][C:3]2=[O:10])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 203884122',3'-Dihydrospiro[cyclopentane-1,1'-inden]-3'-one

Product 1

HCID 203884395'-Nitro-spiro(cyclopentane-1,1'-indan)-3'-oneYield 9,210.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a chilled solution of spiro(cyclopentane-1,1'-indan)-3'-one (16.7 g; 0.09 moles) in conc. sulphuric acid (100 ml) there are added in portions under agitation a solution of potassium nitrate (10 g) in conc. sulphonic acid (30 ml). The temperature should not exceed 10°-15° C. The mixture is kept cold for 1 hour and then put on ice. The crude product is sucked off and thoroughly washed with water. After drying there are obtained 1917 g of a yellow powder (yield 95%), mp. 104° C. A sample is recrystallized from N-hexane and melts at 110° C.

Workup

  1. customexceed 10°-15° C
  2. washthoroughly washed with water
  3. customAfter drying there

Sources & evidence

ORD record
ord-c7f1913b993c4101aeb534a043d381d9
Source dataset
uspto-grants-1979_10
Patent number
US04172093

Reaction notes

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