Toluene → HCID 20229774, compound

HRID 2166758Notes

Reaction equation

HRID 2166758 reaction equation
[C:1]1([CH:7]([OH:17])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22].[H-].[Na+].C1(C)C=CC=CC=1>O>[Cl:22][CH2:21][CH2:20][CH2:19][O:17][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1415431,4-Diphenylbutan-1-ol

Product 1

HCID 20229774HCID 20229774, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 g of 1,4-diphenyl-1-butanol, 42 g of 1-bromo-3-chloropropane, 9.5 g of sodium hydride (65%) and 400 ml of toluene was heated under refluxing for 2 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-(3-chloropropoxy)-1,4-diphenylbutane.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d6e55a0f88549a39e5f9588f5de8fe3
Source dataset
uspto-grants-1983_06
Patent number
US04388469

Reaction notes

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