Water → Dibenzyl ether

HRID 325971Notes

Reaction equation

HRID 325971 reaction equation
N1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=CC=1.[OH2:11]>>[CH2:4]([O:11][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 962WaterHCID 7047Quinoline

Product 1

HCID 7657Dibenzyl ether

Procedure

To a solution of 57.8 g (0.095 mol) α-pivalyl-α-[4-(p-benzyloxyphenylsulfonyl)-phenoxy]-2-chloro-5-amino acetanilide and 13 g quinoline, cooled to 0° C., was added in one portion 45 g (0.095 mol) of the acid chloride B1Cl prepared in Example 4. After stirring 1 h the reaction mixture was poured into 3 L cold water to produce 98 g (after oven drying) crude product. Recrystallization from toluene yielded 84.5 g (0.018 mol) white crystalline dibenzyl ether of the desired coupler. A suspension of 10.4 g (0.01 mol) of this product in 200 mL ethanol and 200 mL tetrahydrofuran was shaken 3 h under 35 psi hydrogen with palladium on charcoal catalyst. Removal of catalyst by filtration, concentration of the filtrate and trituration in hot cyclohexane gave a good yield of coupler Y-2 with the correct elemental analysis.

Workup

  1. customprepared in Example 4
  2. customto produce
  3. custom98 g (after oven drying) crude product
  4. customRecrystallization from toluene

Sources & evidence

ORD record
ord-68b3ef4121564b08a5a44b36ba46cb08
Source dataset
uspto-grants-1984_04
Patent number
US04443536

Reaction notes

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