Toluene → HCID 86602740, compound

HRID 2221424Notes

Reaction equation

HRID 2221424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH2:11]([C@H:13]1[O:15][CH2:14]1)Cl.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C@@H:13]2[O:15][CH2:14]2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 280504-ChloroguaiacolHCID 149428(+)-Epichlorohydrin

Product 1

HCID 86602740HCID 86602740, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a reaction vessel were added 4-chloro-2-methoxyphenol 20.0 g (126 mmol), (S)-epichlorohydrin 23.3 g (252 mmol), benzyl trimethylammonium chloride 0.585 g (3.15 mmol), toluene 40 mL and water 40 mL. To this mixture was dropped an aqueous 24% NaOH solution 31.5 g (189 mmol) in an ice bath, and the mixture was stirred at room temperature for 36 hours. The water layer was removed and the organic layer was washed with an aqueous 5% HCl solution and a 5% NaCl solution successively. The organic layer was taken and the solvent was evaporated to give crude (R)-glycidyl 4-chloro-2-methoxyphenyl ether 22.1 g (yield 87%, chemical purity 93%) as a white solid.

Workup

  1. customThe water layer was removed
  2. washthe organic layer was washed with an aqueous 5% HCl solution
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-612d5fa5b3294921870623fb1ca59863
Source dataset
uspto-grants-2008_05
Patent number
US07368608B2

Reaction notes

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