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

HRID 2264119Notes

Reaction equation

HRID 2264119 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.O.[OH:31][C:32]1[CH:46]=[CH:45][CH:44]=[CH:43][C:33]=1[CH2:34]P(=O)(OCC)OCC>O1CCCC1>[OH:31][C:32]1[CH:46]=[CH:45][CH:44]=[CH:43][C:33]=1[CH:34]=[CH:26][C:25]1[CH:24]=[CH:23][C:22]([N:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:11]2[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1707014-(Bis(p-tolyl)amino)benzaldehydeHCID 23415580Diethyl 2-hydroxybenzylphosphonateHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At first, 14.8 g of potassium tert-butoxide and 50 ml of tetrahydrofuran were put in a reaction vessel having a stirrer, a thermometer and a dropping funnel. Under a nitrogen gas flow, a solution in which 9.90 g of the diethyl 2-hydroxybenzylphosphonate and 5.44 g of 4-(N,N-bis(4-methylphenyl)amino)benzaldehyde were dissolved in tetrahydrofuran was slowly dropped therein at room temperature, and the reaction is further performed for 2 hours at the same temperature. Next, water was added thereto while cooling the reaction product with water, a hydrochloric acid solution with a normal concentration of 2 (i.e., 2N) was added therein to acidize the reaction product, and then tetrahydrofuran was removed by an evaporator. Further, toluene was added thereto 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 then added thereto to dehydrate the toluene phase.

Workup

  1. additionwas slowly dropped
  2. concentrationa hydrochloric acid solution with a normal concentration of 2 (i.e., 2N)
  3. additionwas added
  4. customtetrahydrofuran was removed by an evaporator
  5. additionFurther, toluene was added
  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 then added

Sources & evidence

ORD record
ord-ffba8583eedc4ec682a33cb54d58a976
Source dataset
uspto-grants-2010_12
Patent number
US07855040B2

Reaction notes

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