Hydrochloric Acid → 5-(4-Ethynylphenoxy)pentan-1-ol

HRID 1838016Notes

Reaction equation

HRID 1838016 reaction equation
CC(O)(C)[C:3]#[C:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1.C1(C)C=CC=CC=1.[OH-].[Na+].Cl>C(OCC)(=O)C.O>[C:4]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1)#[CH:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 18751426HCID 18751426, compound

Product 1

HCID 187514205-(4-Ethynylphenoxy)pentan-1-olYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A flask equipped with a stirrer and a thermometer was charged with 5.41 g (20.6 mmol) of 5-[4-(3-methyl-3-hydroxybutyne-1-yl)phenoxy]pentanol and 70 ml of toluene under a nitrogen atmosphere. To the flask, 1.65 g (41.2 mmol) of sodium hydroxide was added, and stirred under reflux for 4 hours. After the completion of the reaction, water, 1N hydrochloric acid, and ethyl acetate were added to the reactant to adjust the pH to an acidity and effect ethyl acetate extraction. The resulting organic phase was washed with NaCl saturated water, dried over anhydrous sodium sulfate, filtered, and concentrated to thereby obtain 4.13 g of 5-(4-ethynylphenoxy)pentanol in the form of a brown oil in a 98% yield.

Workup

  1. customA flask equipped with a stirrer
  2. temperatureunder reflux for 4 hours
  3. additionwere added to the reactant
  4. extractionto an acidity and effect ethyl acetate extraction
  5. washThe resulting organic phase was washed with NaCl saturated water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-99afc5a35d364684ad00f4364911879e
Source dataset
uspto-grants-2004_01
Patent number
US06673267B2

Reaction notes

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