Epichlorohydrin → HCID 72163763, compound

HRID 1639883Notes

Reaction equation

HRID 1639883 reaction equation
CC([CH2:4][C:5]([CH3:7])=[O:6])C.[CH2:8]([CH:10]1[O:12][CH2:11]1)Cl.[C:13]12([C:23]3[CH:28]=[C:27]([C:29]45[CH2:38][CH:33]6[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]6)[CH2:30]4)[CH2:36]5)[C:26]([OH:39])=[CH:25][C:24]=3[OH:40])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.[OH-].[Na+]>C(Cl)(Cl)Cl.CS(C)=O>[C:29]12([C:27]3[CH:28]=[C:23]([C:13]45[CH2:20][CH:19]6[CH2:21][CH:15]([CH2:16][CH:17]([CH2:18]6)[CH2:22]4)[CH2:14]5)[C:24]([O:40][CH2:8][CH:10]4[O:12][CH2:11]4)=[CH:25][C:26]=3[O:39][CH2:4][CH:5]3[O:6][CH2:7]3)[CH2:36][CH:35]3[CH2:37][CH:31]([CH2:32][CH:33]([CH2:34]3)[CH2:38]1)[CH2:30]2

Participants

7

Reactant 4

HCID 7835EpichlorohydrinHCID 7909Methyl Isobutyl KetoneHCID 14798Sodium Hydroxide2×HCID 235558344,6-Bis(adamantyl)resorcinol

Product 1

HCID 72163763HCID 72163763, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

A 500 mL four-necked flask equipped with a reflux condenser, a stirrer, a thermometer, and a nitrogen inlet tube was charged with 57 mL of MIBK, 157 mL of DMSO, and 98 g (1.057 mol) of epichlorohydrin and replaced with nitrogen for 30 minutes. To this solution, 52.01 g (0.137 mol) of 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene synthesized in Example 1 was added, and the flask was replaced with nitrogen for 30 minutes and then heated at 45° C. while stirring. This solution was added with 11.6 g (0.290 mol) of sodium hydroxide over 0.5 hour and the solution was stirred for 1.5 hours. Then, 2.9 g (0.0725 mol) of sodium hydroxide was added and the solution was further stirred for 1 hour. The reaction mixture was cooled to room temperature, and 300 mL of chloroform was added. After washing with 500 mL of water, an aqueous 0.1 mol/L HCl solution was added to the mixture and the organic layer was separated. After further washing with water until the aqueous phase became neutral, the organic layer was concentrated and dried until the weight became constant in a reduced pressure drier at 100° C. to obtain 4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene as a pale-yellow solid (yield: 92%, LC purity: 99.20%, epoxy equivalent: 267, melting point: 193° C.).

Workup

  1. customA 500 mL four-necked flask equipped with a reflux condenser, a stirrer
  2. waitthe flask was replaced with nitrogen for 30 minutes
  3. stirringthe solution was stirred for 1.5 hours
  4. stirringthe solution was further stirred for 1 hour
  5. temperatureThe reaction mixture was cooled to room temperature
  6. washAfter washing with 500 mL of water
  7. additionan aqueous 0.1 mol/L HCl solution was added to the mixture
  8. customthe organic layer was separated
  9. washAfter further washing with water until the aqueous phase
  10. concentrationthe organic layer was concentrated
  11. customdried until the weight
  12. custombecame constant in a reduced pressure drier at 100° C.

Sources & evidence

ORD record
ord-369bdd6743a14bd2b0adfac8cf86d2bc
Source dataset
uspto-grants-2012_02
Patent number
US08110614B2

Reaction notes

Loading…