Sodium Hydroxide → HCID 53706495, compound

HRID 1277573Notes

Reaction equation

HRID 1277573 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH2:13][NH:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:7]([CH3:23])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]1([S:34](Cl)(=[O:36])=[O:35])[CH:29]=[CH:28][CH:27]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:25]=1.[OH-:38].[Na+]>CC(C)=O.O>[C:1]([C:5]1[CH:10]=[C:9]([CH3:12])[C:8]([CH2:13][N:14]([CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])[S:34]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([N:14]([CH2:13][C:8]3[C:7]([CH3:23])=[CH:6][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[C:10]([OH:11])[C:9]=3[CH3:12])[CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])(=[O:32])=[O:31])[CH:25]=2)(=[O:36])=[O:35])=[C:7]([CH3:23])[C:6]=1[OH:38])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 962401,3-Benzenedisulfonyl dichlorideHCID 23452837HCID 23452837, compound

Product 1

HCID 53706495HCID 53706495, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

The procedure of Example 1 is followed using 6-t-butyl-3-(2-ethylhexylaminomethyl)-2,4-dimethylphenol (13.40 grams; 0.042 mole) and 1,3-benzenedisulfonyl chloride (5.5 grams; 0.02 mole) in a mixture of acetone (100 mls) and water (35 mls) while adding a solution of sodium hydroxide (1.76 grams; 0.044 mole) in water (15 mls) and maintaining the temperature at 30°-35° C. The mixture is allowed to stand at ambient temperature for 15 hours. After separating the oily layer, treating the same with ice water to effect crystallization, the solid is filtered to obtain the crude product (15.5 grams; 92% of theoretical). Recrystallization of the crude product from a mixture of benzene and cyclohexane (1 volume: 2 volumes, respectively) affords the desired product (5.5 grams; m.p. 135°-136° C.).

Workup

  1. temperaturemaintaining the temperature at 30°-35° C
  2. customAfter separating the oily layer
  3. additiontreating the same with ice water
  4. customcrystallization
  5. filtrationthe solid is filtered
  6. customto obtain the crude product (15.5 grams; 92% of theoretical)
  7. customRecrystallization of the crude product
  8. additionfrom a mixture of benzene and cyclohexane (1 volume

Sources & evidence

ORD record
ord-0b956809955741cd954ede34b1324526
Source dataset
uspto-grants-1981_07
Patent number
US04278577

Reaction notes

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