Hydrochloric Acid → Styrene Oxide

HRID 436245Notes

Reaction equation

HRID 436245 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C=CC(O)=CC=1)[OH:10].ClOC(C)(C)C.ClCl.Cl.C(Cl)C=C>>[CH2:1]1[O:10][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 7501Styrene2×HCID 7850Allyl chlorideHCID 24526ChlorineHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 7276Styrene Oxide

Procedure

The reaction given in the above example was repeated with styrene in the presence of 0.1 g. of hydroquinone stabilizer. The styrene charged was 49.3 cc (44.8 g., 430 mmole). The t-butyl hypochlorite charged was 48.0 cc (45.0 g., 408 meq. active chlorine), and the total reaction time was three hours. A trace of hydrochloric acid was found in the aqueous product layer. The product pattern in the organic layer was similar to that observed in the allyl chloride reaction. Saponification, as in Example 5, of the organic layer produced styrene oxide.

Sources & evidence

ORD record
ord-e939ede6bbcb4c0b8e4fee7c3d5b91f8
Source dataset
uspto-grants-1977_02
Patent number
US04008133

Reaction notes

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