Sodium Hydroxide → HCID 23452842, compound

HRID 1277574Notes

Reaction equation

HRID 1277574 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([CH3:12])[C:8]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:7]([CH3:33])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:34]1([C:44]2[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=2)[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.[OH-:54].[Na+]>CC(C)=O.O>[C:1]([C:5]1[CH:10]=[C:9]([CH3:12])[C:8]([CH2:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[S:40]([C:37]2[CH:38]=[CH:39][C:34]([C:44]3[CH:49]=[CH:48][C:47]([S:50]([N:14]([CH2:13][C:8]4[C:7]([CH3:33])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:10]([OH:11])[C:9]=4[CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:52])=[O:51])=[CH:46][CH:45]=3)=[CH:35][CH:36]=2)(=[O:42])=[O:41])=[C:7]([CH3:33])[C:6]=1[OH:54])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 76950(1,1'-Biphenyl)-4,4'-disulfonyl dichlorideHCID 23452843HCID 23452843, compound

Product 1

HCID 23452842HCID 23452842, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
35 °C

Procedure

To a stirred solution of 6-t-butyl-3-(octadecylaminomethyl)-2,4-dimethylphenol (9.18 grams; 0.02 mole) in acetone (80 mls) at 35° C. there is added 4,4'-biphenyldisulfonyl chloride (3.5 grams; 0.01 mole) over a period of 20 minutes while maintaining the temperature at 35° C. The mixture is stirred for an additional hour at 35° C. and a solution of 50% caustic soda (1.6 grams; 0.02 mole) in water (8 mls) is added to the reaction mixture which is then allowed to stir at room temperature for 20 hours. The reaction mixture is then treated with water (50 mls) and the resulting precipitate is recovered by filtration, washed with methanol, and dried to obtain the crude product (9.2 grams; 77% of theoretical). Recrystallization of the crude product from n-propanol affords the pure product (4.2 grams; m.p. 208°-210° C.).

Workup

  1. stirringto stir at room temperature for 20 hours
  2. filtrationthe resulting precipitate is recovered by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-fa80c1b5c1724c2babcbc3c523d7f595
Source dataset
uspto-grants-1981_07
Patent number
US04278577

Reaction notes

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