Water → HCID 80741150, compound

HRID 1481985Notes

Reaction equation

HRID 1481985 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]#N)[CH2:2][CH:3]=[CH2:4].[OH-:15].[Na+].[OH2:17]>CCO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([OH:17])=[O:15])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 1183088472-(3-Buten-1-yloxy)benzeneacetonitrile

Product 1

HCID 80741150HCID 80741150, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2-(but-3-en-1-yloxy)phenyl)acetonitrile (1.0 g, 5.34 mmol, 1 equiv) in EtOH (27 mL) was added 10 N NaOH (27 mL). The reaction was heated at reflux for 18 h. Upon cooling to ambient temperature, the reaction was diluted with water and washed with ether. The aqueous layer was acidified with concentrated HCl and extracted with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo to provide the product (0.98 g, 89%) as a viscous pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 11.15-9.85 (m, 1H), 7.30-7.25 (m, 1H), 7.21 (dd, J=7.3, 1.5 Hz, 1H), 6.97-6.91 (m, 1H), 6.89 (d, J=8.3 Hz, 1H), 5.98-5.82 (m, 1H), 5.21-5.14 (m, 1H), 5.10 (dd, J=10.3, 1.5 Hz, 1H), 4.06 (t, J=6.5 Hz, 2H), 3.68 (s, 2H), 2.55 (q, J=6.6 Hz, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. washwashed with ether
  4. extractionextracted with DCM (×3)
  5. dry with materialThe combined DCM extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-947a4ad75940432e9ba40d13d6ba2aa7
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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