2-Methylbenzenesulfonic acid → HCID 19377751, compound

HRID 2210828Notes

Reaction equation

HRID 2210828 reaction equation
[C:1]1(C)[C:2](S(O)(=O)=O)=CC=[CH:5][CH:6]=1.[Cl:12][C:13]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1)(O)[CH2:14][CH2:15][CH3:16].[C:28](=[O:31])(O)[O-:29].[Na+]>O1C=CCCC1>[Cl:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1)[CH2:14][CH2:15][CH2:16][O:29][CH:28]1[CH2:5][CH2:6][CH2:1][CH2:2][O:31]1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 516892Sodium BicarbonateHCID 86749056HCID 86749056, compound

Product 1

HCID 19377751HCID 19377751, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

In 8.7 ml dihydropyran they are added 10 mg p.toluene sulphonic acid (APTS). To this mixture they are added within 30 mn at 60°, 20 g 1-chloro (4-tertbutylphenyl) butanol. After this addition the mixture is still heated at between 60° and 65° C. for 30 mn and kept under stirring for further 90 mn. 0.5 g sodium bicarbonate is thereafter added. The mixture is then stirred for 1 hour. The tetrahydropyranylated derivative is directly used without any further purification.

Workup

  1. additionTo this mixture they are added within 30 mn at 60°
  2. additionAfter this addition the mixture
  3. temperatureis still heated at between 60° and 65° C. for 30 mn
  4. stirringThe mixture is then stirred for 1 hour
  5. customThe tetrahydropyranylated derivative is directly used without any further purification

Sources & evidence

ORD record
ord-6535dbfc0b5945e28f50fa9eb9ae8314
Source dataset
uspto-grants-1995_10
Patent number
US05461059

Reaction notes

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