Hydrochloric Acid → HCID 43214755, compound

HRID 523332Notes

Reaction equation

HRID 523332 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[OH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CN(C=O)C.O>[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)#[N:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 794355-Bromopentanenitrile

Product 1

HCID 43214755HCID 43214755, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

21.0 g (130 mmol) of 5-bromopentanenitrile, 15.2 g (100 mmol) of methyl 4-hydroxybenzoate and 28 g (200 mmol) of potassium carbonate are dissolved in 100 mL of DMF. The mixture is heated to 80° C. overnight. 100 mL (100 mmol) of a 1N NaOH solution is added to the above mixture. The suspension is heated at reflux for 30 min until the reaction is completed. The reaction mixture is allowed to cool down to room temperature and thrown onto cold water. The solution is carefully acidified with a 25% HCl solution and is stirred for 15 min. The product is filtrated off, washed with water and dried overnight under vacuum to give 19.3 g of 4-(4-cyanobutoxy)benzoic acid as a white solid.

Workup

  1. temperatureThe suspension is heated
  2. temperatureat reflux for 30 min until the reaction
  3. temperatureto cool down to room temperature
  4. filtrationThe product is filtrated off
  5. washwashed with water
  6. customdried overnight under vacuum

Sources & evidence

ORD record
ord-6d7f69e4010f4f18b49e598c126a0236
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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