p-Toluenesulfonic acid → HCID 22504594, compound

HRID 1368933Notes

Reaction equation

HRID 1368933 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 1235044-Hydroxy-4'-chlorobenzophenone

Product 1

HCID 22504594HCID 22504594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-4′-hydroxybenzophenone (50 g, 0.215 mol) is dissolved in dichloromethane (400 ml). 3,4-Dihydro-2H-pyran (21.7 g, 0.257 mol) and a catalytic amount of p-toluenesulfonic acid are added to the solution. The solution is stirred for 6 hours at room temperature and then allowed to stand over night. 1 N aqueous sodium hydroxide solution (100 ml) is added to the reaction mixture and stirred for 15 minutes. Organic layer is separated and washed twice with 1 N aqueous sodium hydroxide solution and once with water. Dichloromethane solution is dried and evaporated to dryness. Yield 68.6 g.

Workup

  1. waitto stand over night
  2. stirringstirred for 15 minutes
  3. customOrganic layer is separated
  4. washwashed twice with 1 N aqueous sodium hydroxide solution and once with water
  5. dry with materialDichloromethane solution is dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1cf4dd82b8af4014a0a161bd7d290dc6
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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