Potassium Hydroxide → N-(3-methyl-4-hydroxy-5-tert-butylphenylthiomethyl)phthalimide

HRID 1383031Notes

Reaction equation

HRID 1383031 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:13])[CH:5]=[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:7]=1[OH:8].[OH-].[K+].Cl[CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>>[CH3:1][C:2]1[CH:3]=[C:4]([S:13][CH2:17][N:18]2[C:19](=[O:28])[C:20]3=[CH:27][CH:26]=[CH:25][CH:24]=[C:21]3[C:22]2=[O:23])[CH:5]=[C:6]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:7]=1[OH:8]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 87154ChloromethylphthalimideHCID 13547656HCID 13547656, compound

Product 1

HCID 14047795N-(3-methyl-4-hydroxy-5-tert-butylphenylthiomethyl)phthalimideYield 46.3%

Procedure

The procedure of Example 1 was repeated using 8.46 grams of 3-methyl-4-hydroxy-5-tert-butylbenzenethiol, 1.72 grams of potassium hydroxide, and 8.43 grams of N-(chloromethyl)phthalimide. Recrystallization from ethyl acetate-heptane afforded 7.1 grams of product with m.p. 114°-116° C.

Workup

  1. customRecrystallization from ethyl acetate-heptane

Sources & evidence

ORD record
ord-dee18dd548ae459485c9c510fed762b8
Source dataset
uspto-grants-1989_02
Patent number
US04808644

Reaction notes

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