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Water → HCID 20213775, compound

HRID 1906032
Notes
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Reaction equation

HRID 1906032 reaction equation
[OH:1][C:2]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[OH:18])=[O:5].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl.[OH-:30].[Na+].[OH2:32]>[Cl-].C[N+](C)(C)C>[CH2:25]([O:1][C:2]1[CH:23]=[C:22]([O:24][CH2:25][CH:27]2[O:29][CH2:28]2)[CH:21]=[CH:20][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:3][CH:2]2[O:30][CH2:23]2)=[CH:13][C:12]=1[O:18][CH2:4][CH:6]1[O:32][CH2:7]1)=[O:5])[CH:27]1[O:29][CH2:28]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water3×HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 283375Hexane-1,6-dione, 1,6-bis(2,4-dihydroxyphenyl)-

Product 1

HCID 20213775HCID 20213775, compound

Reagents, catalysts & solvents 1

HCID 6379
Tetramethylammonium chloride
Catalyst

Conditions

Temperature
60 °C

Procedure

18.16 g (0.055 mole) of 1,4-bis-(2',4'-dihydroxybenzoyl)-butane, 86.84 g (0.938 mole) of epichlorohydrin and 0.97 g of 50% aqueous tetramethylammonium chloride solution are initially placed in a 350 ml sulfonation flask equipped with a stirrer, a thermometer, a condenser, a dropping funnel and a water separator, and are heated at 105°-110° C. After a reaction time of 4 hours the reaction mixture is cooled to 60° C.; 20.21 g (0.253 mole) of 50% aqueous sodium hydroxide solution are then added with simultaneous removal of water from the system. The resulting suspension is treated with water, and the organic phase is washed with water, dried over sodium sulphate and concentrated. This gives 28.62 g (93.84% of theory) of a red, viscous resin.

Workup

  1. customequipped with a stirrer
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9008c956e24f4443874f47cd15f0a104
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04649181

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes