1-Methoxy-1,3,5-cycloheptatriene → 7-Methoxycycloheptatriene

HRID 1413237ノート

反応式

HRID 1413237 の反応式
[CH3:1][O:2][C:3]1[CH2:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[B-](F)(F)(F)F.C1C=C[CH+]C=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][CH:3]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=[CH:4]1

参加物

5

反応物 3

HCID 1509381-Methoxy-1,3,5-cycloheptatrieneHCID 152926Cycloheptatrienylium, tetrafluoroborate(1-) (1:1)HCID 516892Sodium Bicarbonate

生成物 1

HCID 1371707-Methoxycycloheptatriene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

An improved multi-step process for synthesizing the liquid irritant 1-methoxycycloheptatriene through the steps of reacting cycloheptatrienyl tetrafluoroborate in aqueous solution with methanol and sodium bicarbonate to produce 7-methoxycycloheptatriene, thermally isomerizing the 7-methoxycycloheptatriene to 3-methoxycycloheptatriene by heating at 150° C. for 2 hours and isomerizing the 3-methoxycycloheptatriene to 1-methoxycycloheptatriene by acid, catalyzed rearrangement employing methanolic hydrogen chloride followed by neutralization with sodium bicarbonate, filtration and fractional distillation to give the final product the improvement comprising the step of utilizing a polymerization/condensation inhibitor to increase the overall yield and purity of the 1-methoxycycloheptatriene product. The overall yield and purity of the product can further be increased through the step of conducting the thermal isomerization of 7-methoxy to 3- and 1-methoxycycloheptatriene at 180° C. under reduced pressure, e.g., by heating in a sealed reactor.

出典と根拠

ORDレコード
ord-9a5b048391104da6a8101d91483d455b
出典データセット
uspto-grants-1981_02
特許番号
US04249025

反応ノート

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