Acetone → Sodium Hydroxide

HRID 1739365Notes

Reaction equation

HRID 1739365 reaction equation
CC(C)=[O:3].C(C(C)=O)C.[Br:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([Br:18])[C:12]=1[O-:19].[Na+:20]>O>[OH-:3].[Na+:20].[Br:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([Br:18])[C:12]=1[O-:19].[Na+:20]

Participants

6

Reactant 3

HCID 180AcetoneHCID 6569Methyl Ethyl KetoneHCID 23666164Phenol, 2,4,6-tribromo-, sodium salt

Product 2

HCID 14798Sodium HydroxideHCID 23666164Phenol, 2,4,6-tribromo-, sodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It has been found that a liquid ketone such as acetone or methyl ethyl ketone when present in this reaction mixture tends to ensure that the desired tris(2,4,6-tribromophenoxy)-s-1,3,5-triazine product is formed in high purity. In experiments wherein a refluxing mixture of water and an alkanol (methanol), was used as the reaction medium for step d), it was found that some of the chloro groups in the cyanuric chloride reacted with the methanol to form bis-(tribromophenoxy)-methoxy-s-1,3,5-triazine as an impurity. On the other hand, when acetone or methyl ethyl ketone was used as the organic solvent in step d), the chloro groups were found to react exclusively with the sodium 2,4,6-tribromophenolate despite of the presence of a large amount of water in the reaction mixture which was carried over from the prior bromination step and the prior use of aqueous NaOH to form the sodium 2,4,6-tribromophenolate.

Sources & evidence

ORD record
ord-39c5db163e5e46e8948310c9d16b607c
Source dataset
uspto-grants-1999_10
Patent number
US05965731

Reaction notes

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