1,3-Butadiene → HCID 10821569, compound

HRID 359652

Reaction equation

HRID 359652 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.[CH2:11]=[CH:12][CH:13]=[CH2:14]>>[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]2[CH:6]([C:7](=[O:9])[CH:8]=1)[CH2:14][CH:13]=[CH:12][CH2:11]2

Participants

3

Reactant 2

HCID 78451,3-ButadieneHCID 761462-Methoxy-1,4-benzoquinone

Product 1

HCID 10821569HCID 10821569, compound

Procedure

Little is known, however, concerning the reaction of methoxy and 2,6-dimethoxy-p-benzoquinone. (The latter can be generated from lignin). It has been shown that methoxy-p-benzoquinone will react with 1,3-butadiene to give 2-methoxy-4a,5,8,8a-tetrahydronapthoquinone [G. I. Birnbaum, J. Org. Chem., 25, 1660-1, (1960)]and with 2,3-dimethyl-1,3-butadiene to give 5,8-dihydro-2-methoxy-6,7-dimethyl -1,4-napthoquinone [M. F. Ansell, J. Chem. Soc., 3020, (1963)]. A more recent publication has shown that 2,6-dimethoxy-p-benzoquinone can be combined with isoprene to give a mixture of 2-methoxy-6-methyl-1,4-napthoquinone and 2-methoxy-7-methyl-1,4-napthoquinone [I.-M. TegmoLarsson, Tetra. Letters, 22, 2043-6, (1981)].

Sources & evidence

ORD record
ord-f82020de4d1f4ab992680e62eda26a01
Source dataset
uspto-grants-1991_03
Patent number
US05002634

Linked notes

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