p-Toluenesulfonic acid → HCID 70655408, compound

HRID 77340Notes

Reaction equation

HRID 77340 reaction equation
O[CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[O:4]1.[C:21]1(C)[CH:26]=[CH:25][C:24]([S:27](O)(=O)=O)=[CH:23][CH:22]=1.C1(S)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:13]([N:10]1[CH2:9][CH2:8][C:5]2([O:4][CH:3]([CH2:2][S:27][C:24]3[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=3)[CH2:7][O:6]2)[CH2:12][CH2:11]1)[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7969ThiophenolHCID 667015182-Hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane2×

Product 1

HCID 70655408HCID 70655408, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (Compound 1, 50 gm, 0.18 mole) and Para Toluenesulfonic Acid (PTSA, 2 gm) were dissolved in toluene (350 ml) at room temperature. 20 gm of thiophenol was added drop wise to the above solution. The reaction was refluxed for 13 hrs at reflux temperature. The solvent was distilled off to get the light brown solid product with a melting point of 58° C. The yield of the product was 95%.

Workup

  1. temperatureThe reaction was refluxed for 13 hrs
  2. temperatureat reflux temperature
  3. distillationThe solvent was distilled off
  4. customto get the light brown solid product with a melting point of 58° C

Sources & evidence

ORD record
ord-054d4a7a395e4bf7aa1e7ee4c889894b
Source dataset
uspto-grants-2014_09
Patent number
US08841296B2

Reaction notes

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