Hydrochloric Acid → 2-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenol

HRID 420422Notes

Reaction equation

HRID 420422 reaction equation
[K].CC(C)([O-])C.[OH:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH2:10]P(=O)(OCC)OCC.[C:23]1([CH3:45])[CH:28]=[CH:27][C:26]([N:29]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.Cl>O1CCCC1.O>[OH:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH:10]=[CH:44][C:41]1[CH:40]=[CH:39][C:38]([N:29]([C:30]2[CH:37]=[CH:36][C:33]([CH3:34])=[CH:32][CH:31]=2)[C:26]2[CH:27]=[CH:28][C:23]([CH3:45])=[CH:24][CH:25]=2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1707014-(Bis(p-tolyl)amino)benzaldehydeHCID 23415580Diethyl 2-hydroxybenzylphosphonateHCID 50987170Potassium tertbutoxide

Product 1

HCID 666592702-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenolYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

14.8 g of kalium-tert-butoxide and 50 ml of tetrahydrofuran were put in a reaction reservoir having a mixer, a thermometer and a dropping funnel. Under a nitrogen stream, a solution wherein 9.90 g of the diethyl 2-hydroxybenzylphosphonate and 5.44 g of 4-(di-para-tolylamino)benzaldehyde were dissolved in tetrahydrofuran was slowly dropped therein at a room temperature, and the reaction therein is further performed for 2 hrs at the same temperature. Then, water was added therein while cooling the reaction product with water, a hydrochloric acid solution having a normal concentration of 2 was added therein to acidize the reaction product, and the tetrahydrofuran was removed by an evaporator to extract a crude product with toluene. The toluene phase was washed with water, a sodium hydrogen carbonate solution and a saturated saline in this order, and magnesium sulfate was further added thereto to dehydrate the toluene phase. After filtered, the toluene was removed therefrom to prepare an oily crude product, and the oily crude product was further column-refined with silica gel to crystallize 5.09 g of 2-hydroxy-4′-(di-para-tolylamino)stilbene in hexane at a yield of 72%, having a boiling point of 136.0 to 138.0° C.

Workup

  1. additionwas slowly dropped
  2. customat a room temperature, and the reaction
  3. concentrationa normal concentration of 2
  4. additionwas added
  5. customthe tetrahydrofuran was removed by an evaporator
  6. extractionto extract a crude product with toluene
  7. washThe toluene phase was washed with water
  8. additiona sodium hydrogen carbonate solution and a saturated saline in this order, and magnesium sulfate was further added
  9. filtrationAfter filtered
  10. customthe toluene was removed
  11. customto prepare an oily crude product
  12. customto crystallize 5.09 g of 2-hydroxy-4′-(di-para-tolylamino)stilbene in hexane at a yield of 72%

Sources & evidence

ORD record
ord-5416d8c340f7492298cbf5fcc70ecd58
Source dataset
uspto-grants-2012_01
Patent number
US08097394B2

Reaction notes

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