Water → HCID 178487220, compound

HRID 280161Notes

Reaction equation

HRID 280161 reaction equation
[C:1]([CH:3]1[C:6]2=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]2[CH2:4]1)#N.[OH-:13].[K+].[OH2:15]>C(O)C.CCOCC>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]2[CH:4]=[C:3]([C:1]([OH:15])=[O:13])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 12238660Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-

Product 1

HCID 178487220HCID 178487220, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-Cyano-5-methoxybenzocyclobutene (29 g) is stirred with saturated KOH in ethanol (180 ml) for about 12 hours under nitrogen at RT. Water (60 ml) is added to the reaction mixture which is refluxed for about 3 hours. The mixture is cooled to RT, diluted with water, washed with ether and the aqueous layer acidified forming an oil. The oil is dissolved in ether and the ethereal solution washed, dried over Na2SO4, filtered and evaporated in vacuo affording the desired product as an oil.

Workup

  1. temperatureis refluxed for about 3 hours
  2. washwashed with ether
  3. customthe aqueous layer acidified forming an oil
  4. washthe ethereal solution washed
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d2bf00a0ce748859ba871c82926861f
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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