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

HRID 428841Notes

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 2.6 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 8-22).

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-bc6bf07b056d44c08d28be2cf0609df0
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313305B1

Reaction notes

Loading…