Water → 11-(p-Tolyloxy)undecan-1-ol

HRID 444610Notes

Reaction equation

HRID 444610 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[CH:14]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]([CH3:21])[CH:15]=1.[OH-].[K+].O>C(O)C.C(Cl)Cl>[C:16]1([CH3:21])[CH:15]=[CH:14][C:19]([O:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 14797Potassium HydroxideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 6754196011-(p-Tolyloxy)undecan-1-olYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The 11-bromoundecan-1-ol 15 (3.68 g) and 4.88 g of p-cresol were dissolved in 20 ml of ethanol, and 2.57 g of potassium hydroxide was added to that, followed by 24-hour refluxing. After cooled to room temperature, the reaction solution is moved into a separating funnel, and 100 ml of ion-exchange water and 50 ml of methylene chloride were added so as to cause separation. After the organic phase was collected and was dehydrated with sodium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The resultant solid was re-dissolved in 50 ml of toluene, and was washed twice with 10 wt % of aqueous potassium hydroxide solution, and was then washed with 50 ml of saturated saline. After that, the organic phase was collected, and was dehydrated with sodium sulfate. The desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure, to obtain 4.08 g of 11-(p-tolyloxy)undecan-1-ol 16, which is a white solid.

Workup

  1. waitfollowed by 24-hour
  2. temperaturerefluxing
  3. customthe reaction solution is moved into a separating funnel
  4. customseparation
  5. customAfter the organic phase was collected
  6. customthe desiccant agent was removed by filtration
  7. distillationthe solvent of the filtrate was distilled away under reduced pressure
  8. dissolutionThe resultant solid was re-dissolved in 50 ml of toluene
  9. washwas washed twice with 10 wt % of aqueous potassium hydroxide solution
  10. washwas then washed with 50 ml of saturated saline
  11. customAfter that, the organic phase was collected
  12. customThe desiccant agent was removed by filtration
  13. distillationthe solvent of the filtrate was distilled away under reduced pressure

Sources & evidence

ORD record
ord-817bc86595094b03b75420726869548e
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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