Water → 2-Chloro-4,5-bis-[(2-methoxyethoxy)-methoxy]-(1,2-epoxy)-styrol

HRID 727416Notes

Reaction equation

C([O:5]O)(C)(C)C.C1(C)C=CC=CC=1.[Cl:14][C:15]1[CH:22]=[C:21]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[C:20]([O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:19][C:16]=1[CH:17]=[CH2:18].O>C(Cl)Cl.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.O=[V]>[Cl:14][C:15]12[O:5][C:16]1([CH:19]=[C:20]([O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:21]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:22]2)[CH:17]=[CH2:18]

Participants

Conditions

Temperature: 0 °C

Procedure

19 g of vanadylacetylacetonate in solution of 50 ml of methylene chloride were cooled to 0° C. and 3.5 ml of terbutyl hydroperoxide in a toluene solution (3M/l) were added over 30 minutes. The mixture was stirred for 20 minutes at 0° C. and 2.63 g of the product of Stage D in solution in 10 ml of methylene chloride were added. The reaction mixture was stirred for 3 hours at ambient temperature and 30 ml of water were added. The organic phase was separated and the solvent was eliminated under reduced pressure. The residue was chromatographed on silica (eluant: methylene chloride-acetone 8-2) to obtain 21.8 g of the expected product with a Rf=0.35 (CH2Cl2 -acetone 8-2).

Workup

stirringThe reaction mixture was stirred for 3 hours at ambient temperature
customThe organic phase was separated
customThe residue was chromatographed on silica (eluant: methylene chloride-acetone 8-2)

Sources & evidence

ORD record: ord-f0ae8adaa28a46d2b296fff54604b4df
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712266

Reaction notes

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