Hydrochloric Acid → HCID 14650331, compound

HRID 523335Notes

Reaction equation

HRID 523335 reaction equation
[OH-].[Na+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].[CH2:11]([C:14]#[N:15])[CH2:12]Br.Cl.O.O1CCOC[CH2:19]1>>[OH:4][C:3]1[CH:10]=[CH:9][C:7]([O:8][CH2:19][CH2:12][CH2:11][C:14]#[N:15])=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14798Sodium HydroxideHCID 170203-BromopropionitrileHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 14650331HCID 14650331, compound

Procedure

To a solution of 1.7 g of NaOH in 80 ml of H2O:dioxane 1:1, 2.2 g (20 mmol) of hydroquinone are added. The solution is stirred for 15 min. Then, 3.5 g (24 mmol) of 3-bromopropanitrile is dropwise added. After complete addition, the mixture is heated up to reflux and stirred for 24 hours. 45 mL of a 1N HCl solution is added to the above mixture. The solution is extracted with ethylacetate and concentrated under reduced pressure to give 2.8 g of 4-(4-hydroxyphenoxy)butanenitrile which is used without further purification.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is heated up
  3. temperatureto reflux
  4. stirringstirred for 24 hours
  5. extractionThe solution is extracted with ethylacetate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2b7736e65be48fc9a80331d6dde6736
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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