1,3-Butadiene → 1,3-Butadiene

HRID 276157Notes

Reaction equation

HRID 276157 reaction equation
[CH:1]1[C:6]([C:7]([OH:19])(C(Cl)(Cl)Cl)[C:8]2C=CC(Cl)=CC=2)=[CH:5]C=[C:3](Cl)[CH:2]=1.C=CC=C>>[CH2:6]=[CH:1][CH:2]=[CH2:3].[O:19]1[CH2:8][CH:7]1[CH:6]=[CH2:5]

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 8268Dicofol

Product 2

HCID 78451,3-ButadieneHCID 13586Vinyloxirane

Procedure

CPCA is derived from 1,3-butadiene by a sequence of four reactions. Monoepoxidation of 1,3-butadiene produces 3,4-epoxy-1-butene (EPB) as described in U.S. Pat. Nos. 4,897,498 and 4,950,773. This epoxide is isomerized to 2,5-DHF (U.S. Pat. Nos. 5,082,956 and 5,315,019) which is isomerized to 2,3-DHF (U.S. Pat. Nos. 5,254,701 and 5,536,851). Finally, 2,3-DHF is isomerized to CPCA (C. L. Wilson, J. Amer. Chem. Soc., 69, 3002 (1947) and U.S. Pat. No. 5,502,257).

Sources & evidence

ORD record
ord-5cb8ae1cdedb45b5a7df1440ce203d52
Source dataset
uspto-grants-2002_03
Patent number
US06353140B1

Reaction notes

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