Epichlorohydrin → HCID 20135273, compound

HRID 1463108Notes

Reaction equation

HRID 1463108 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH2:21][CH:22]=[CH2:23])[CH:15]=2)([CH3:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl.[OH-].[Na+].[CH3:31][O:32][CH2:33][CH2:34]O>>[CH2:21]([C:16]1[CH:15]=[C:14]([C:11]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:34][CH:33]3[O:32][CH2:31]3)=[C:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=2)([CH3:13])[CH3:12])[CH:19]=[CH:18][C:17]=1[O:20][CH2:24][CH:26]1[O:28][CH2:27]1)[CH:22]=[CH2:23]

Participants

5

Reactant 4

HCID 7835EpichlorohydrinHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 74457Phenol, 4,4'-(1-methylethylidene)bis(2-(2-propen-1-yl)-

Product 1

HCID 20135273HCID 20135273, compoundYield 604.4%

Conditions

Temperature
60 °C

Procedure

2,2-Bis(3-allyl-4-hydroxyphenyl)propane (308 g) was mixed with 2-methoxyethanol (10 g) and epichlorohydrin (740 g) and heated to 60° C. Sodium hydroxide flake (80 g) was added portionwise over 3 hours, and the mixture was stirred for a further 1/2 hour, also at 60° C. The mixture was filtered, the residue being washed with toluene, and the filtrate was evaporated to remove the solvents and the excess of epichlorohydrin. The concentrated product was filtered once more to give 334 g of 2,2-bis(3-allyl-4-(glycidyloxy)phenyl)propane, having an epoxide content of 4.03 equiv./kg and 4.5 allyl double bond equiv./kg.

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue being washed with toluene
  3. customthe filtrate was evaporated
  4. customto remove the solvents
  5. filtrationThe concentrated product was filtered once more

Sources & evidence

ORD record
ord-f7f184fc8c6648b4b89b8457daf474b7
Source dataset
uspto-grants-1984_07
Patent number
US04463169

Reaction notes

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