Sodium Hydroxide → HCID 21469826, compound

HRID 2295147Notes

Reaction equation

HRID 2295147 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:27][CH2:28][CH2:29][CH2:30][Cl:31]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=[CH:19][CH:20]=2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 10614463HCID 10614463, compound

Product 1

HCID 21469826HCID 21469826, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

Combine 4-benzyloxy-4'-hydroxybenzophenone (9.12 g, 30.0 mmol) and sodium hydroxide (1.8 g, 45 mmol) in water (35 mL). Add tetrabutylammonium hydrogensulfate (1.02 g, 3.0 mmol). Add 1-bromo-4-chlorobutane (5.2 mL, 45 mmol). Heat to reflux. After 3 hours, cool the reaction mixture to give a solid. Collect the solid by filtration, rinse with water, and dry to give 4-benzyloxy-4'-(4-chlorobutyloxy)benzophenone: Rf =0.32 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool the reaction mixture
  3. customto give a solid
  4. customCollect the solid
  5. filtrationby filtration
  6. washrinse with water
  7. customdry

Sources & evidence

ORD record
ord-75aaf8f95769411cb2155f6bacd3cf3b
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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