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Water → Bis(4-allyloxyphenyl)sulfone

HRID 1982654
Notes
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Reaction equation

HRID 1982654 reaction equation
O.[OH-].[Na+].[S:4]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH2:21](Br)[CH:22]=[CH2:23].[C:25]1(C)[CH:30]=CC=C[CH:26]=1>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC>[CH2:21]([O:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:30][CH:25]=[CH2:26])=[CH:16][CH:15]=2)(=[O:6])=[O:5])=[CH:8][CH:9]=1)[CH:22]=[CH2:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6626Bisphenol SHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 257484Bis(4-allyloxyphenyl)sulfone

Reagents, catalysts & solvents 1

HCID 21218
Trioctylmethylammonium chloride
Catalyst

Procedure

A flask was charged with 150 parts of water, 150 parts of toluene, 12 parts of caustic soda, and 25 parts of 4,4'-sulfonyldiphenol, and the resulting mixture was dissolved completely to form a solution. To this solution were added 1 part of trioctylmethylammonium chloride (a phase transfer catalyst) and then 36.3 parts of allyl bromide. The resulting solution was reacted at 50° to 60° C. for 15 hours, and toluene was steam-distilled to obtain pale yellow crystals. After filtration, the crystals were washed with 100 parts of methanol to obtain white crystals of bis(4-allyloxyphenyl) sulfone of formula (4). Yield: 30.5 parts (91.2%), m.p.: 143° to 146° C.

Workup

  1. dissolutionthe resulting mixture was dissolved completely
  2. customto form a solution
  3. customThe resulting solution was reacted at 50° to 60° C. for 15 hours
  4. distillationtoluene was steam-distilled
  5. customto obtain pale yellow crystals
  6. filtrationAfter filtration
  7. washthe crystals were washed with 100 parts of methanol

Sources & evidence

ORD record
ord-4613b84a31474978b4380d088f88d79b
Source dataset
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04596997

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes