Sodium Hydroxide → 11-(p-Hydroxyphenoxy)undecanoic acid

HRID 634597Notes

Reaction equation

HRID 634597 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21260204Ethyl 11-(p-hydroxyphenoxy)undecanoate

Product 1

HCID 2125993511-(p-Hydroxyphenoxy)undecanoic acidYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 500 ml flask equipped with a stirrer and a condenser were charged 32.2 g of ethyl 11-(p-hydroxyphenoxy)undecanoate synthesized in Synthetic example 2, 100 g of a 10% aqueous sodium hydroxide solution and 100 ml of ethanol, and the mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was concentrated, poured into 600 ml of a 2% aqueous hydrochloric acid solution and precipitated crystals were collected by filtration. The resulting crystals were washed with distilled water and recrystallized from acetonitrile to obtain 20.2 g of the title compound.

Workup

  1. customIn a 500 ml flask equipped with a stirrer and a condenser
  2. temperaturethe mixture was refluxed for 2 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated
  5. additionpoured into 600 ml of a 2% aqueous hydrochloric acid solution
  6. customprecipitated crystals
  7. filtrationwere collected by filtration
  8. washThe resulting crystals were washed with distilled water
  9. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-a0f803c3f84043ea8b0dc8ec6f4c2c14
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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