Epichlorohydrin → HCID 87322565, compound

HRID 2422993Notes

Reaction equation

HRID 2422993 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][C:10]([C:18]5[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH:25]6[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]6)[CH:19]=5)([CH2:11]4)[CH2:9]2)[CH2:15]3)=[CH:4][C:3]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[CH2:37]([CH:39]1[O:41][CH2:40]1)Cl.[OH-].[Na+].CC([CH2:47][C:48]([CH3:50])=[O:49])C>CS(C)=O>[CH2:37]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][C:10]([C:18]5[CH:23]=[CH:22][C:21]([O:24][CH2:47][CH:48]6[O:49][CH2:50]6)=[C:20]([CH:25]6[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]6)[CH:19]=5)([CH2:11]4)[CH2:9]2)[CH2:15]3)=[CH:4][C:3]=1[CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[CH:39]1[O:41][CH2:40]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 7909Methyl Isobutyl Ketone2×HCID 14798Sodium HydroxideHCID 12081209HCID 12081209, compound

Product 1

HCID 87322565HCID 87322565, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

In a mixed solvent composed of 14 mL of MIBK and 30 mL of DMSO, 10 g (20.6 mmol) of 1,3-bis(4-hydroxy-3-cyclohexylphenyl)adamantane (product of Honshu Chemical Industry Co., Ltd.) were dissolved, to which 15 g of epichlorohydrin were added. The mixture was then heated to 45° C. with stirring, added with 2.0 g (50 mmol) of sodium hydroxide over 0.5 hour, and further stirred for 6 hours. Thereafter, the obtained reaction liquid was cooled to room temperature and added with 50 mL of MIBK. The organic layer was washed with 50 mL of pure water, then one time with 50 mL of 0.1 mol/L hydrochloric acid and twice with 50 mL of pure water. The organic phase was separated and concentrated to give 12.2 g of yellow viscous liquid containing BCHP13-EPO.

Workup

  1. additionwere added
  2. stirringfurther stirred for 6 hours
  3. customThereafter, the obtained reaction liquid
  4. temperaturewas cooled to room temperature
  5. washThe organic layer was washed with 50 mL of pure water
  6. customThe organic phase was separated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f60beaabda144565b2c37a64dc0ca8f6
Source dataset
uspto-grants-2011_06
Patent number
US07960483B2

Reaction notes

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