Hydroquinone → HCID 69891747, compound

HRID 2088119Notes

Reaction equation

HRID 2088119 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22](#[N:25])[CH:23]=[CH2:24].C1(C=CC(O)=CC=1)O.C([O-])(O)=O.[Na+]>O1CCOCC1.C(N(CC)CC)C>[CH2:2]([N:9]1[C@@H:14]2[CH:23]([C:22]#[N:25])[CH2:24][C@@:10]1([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11](=[O:15])[CH:12]=[CH:13]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 7855AcrylonitrileHCID 516892Sodium BicarbonateHCID 21931695N-benzyl-3-hydroxy-2-phenylpyridinium bromide

Product 1

HCID 69891747HCID 69891747, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-benzyl-3-hydroxy-2-phenylpyridinium bromide (150 g, 0.44 mol), acrylonitrile (300 ml), triethylamine (95 ml), hydroquinone (125 mg) and 1,4-dioxane (650 ml) was heated at reflux (80° C.) for 68 hours and cooled to room temperature. The reaction mixture was poured onto saturated aqueous NaHCO3 (1 l) and extracted into an 1:1 mixture of iso-hexane:diethyl ether (3×500 ml). The combined organic extracts were dried (Na2SO4) and concentrated to give a mixture of regio and stereoisomers in the ratio

Workup

  1. temperaturewas heated
  2. temperaturecooled to room temperature
  3. extractionextracted into an 1:1 mixture of iso-hexane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give
  7. additiona mixture of regio and stereoisomers in the ratio

Sources & evidence

ORD record
ord-67eb3ab2255445999711185ed4c0af5c
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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