Ethanol → 4-(6-Hydroxyhexyloxy)-4'-nitrobiphenyl

HRID 2082112Notes

Reaction equation

HRID 2082112 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C(O)C.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]>O>[OH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 779706-Bromo-1-hexanolHCID 1380784-Hydroxy-4'-nitrobiphenyl

Product 1

HCID 197795694-(6-Hydroxyhexyloxy)-4'-nitrobiphenylYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 71 g potassium hydroxide in 300 ml water is dripped under reflux, into a mixture of 215 g 4-hydroxy-4'-nitrobiphenyl (see Example 3) and 4000 ml ethanol. Then, 217 g 6-bromohexanol is added, subsequently, the mixture is heated under reflux for 15 h. After cooling, the solvent is removed in a vacuum and the residue is slurried up with water dried. The raw product is filtered off, washed neutral with water and recrystallized from ethanol (melting point: 119° C.); yield: 65%.

Workup

  1. temperaturesubsequently, the mixture is heated
  2. temperatureunder reflux for 15 h
  3. temperatureAfter cooling
  4. customthe solvent is removed in a vacuum
  5. customdried
  6. filtrationThe raw product is filtered off
  7. washwashed neutral with water
  8. customrecrystallized from ethanol (melting point: 119° C.)

Sources & evidence

ORD record
ord-2bf3f63d5eec4f17a64613f4c34219d5
Source dataset
uspto-grants-1993_02
Patent number
US05187237

Reaction notes

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