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1,2-Epoxybutane → 9-(2,6-Dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

HRID 28104
ノート
印刷プレビュー

反応式

HRID 28104 の反応式
[Cl-].[Cl:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([CH3:31])=[C:25]([Cl:32])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC1C(C)=C(OC)C=C(Cl)C=1CCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:65]([O:67][C:68](=[O:79])[CH:69]=[C:70]([CH3:78])[CH:71]=[CH:72][CH:73]=[C:74]([CH:76]=O)[CH3:75])[CH3:66].C1OC1CC>C1(C)C=CC=CC=1.CCCCCC>[CH2:65]([O:67][C:68](=[O:79])[CH:69]=[C:70]([CH3:78])[CH:71]=[CH:72][CH:73]=[C:74]([CH3:76])[CH:75]=[CH:5][C:4]1[C:25]([Cl:32])=[C:26]([CH3:31])[C:27]([O:29][CH3:30])=[CH:28][C:3]=1[Cl:2])[CH3:66]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 78341,2-EpoxybutaneHCID 11776TriphenylphosphineHCID 234625772,6-Dichloro-4-methoxy-3-methyl-benzyl chlorideHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoateHCID 86736665(2,6-Dichloro-3-methyl-4-methoxybenzyl) triphenyl phosphonium chloride

生成物 1

HCID 127591
9-(2,6-Dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

試薬・触媒・溶媒 1

HCID 21889329Toluene hexane溶媒

実験手順

100 g. of 2,6-dichloro-4-methoxy-5-methyl-benzyl-triphenylphosphonium chloride, prepared from 52 g. of 2,6-dichloro-4-methoxy-3-methyl-benzyl chloride and 57 g. of triphenylphosphine, are treated with 42 g. of 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester. After the addition of 120 ml. of 1,2-butylene oxide, the resulting mixture is heated to 80°-85° C. for 4 hours while stirring. The mixture is diluted with toluene/hexane (1:1 parts by volume) and exhaustively extracted with methanol/water (60:40 parts by volume). The resulting solution is evaporated under reduced pressure. The oily residue is purified by adsorption on silica gel using toluene for the elution. 9-(2,6-dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester is obtained from the eluate and melts at 100°-101° C. after recrystallization from benzene/hexane (50:50 parts by volume).

後処理

  1. additionAfter the addition of 120 ml
  2. extractionexhaustively extracted with methanol/water (60:40 parts by volume)
  3. customThe resulting solution is evaporated under reduced pressure
  4. customThe oily residue is purified by adsorption on silica gel
  5. washfor the elution

出典と根拠

ORDレコード
ord-c89e883b75a84e41afb4b1f8004b6ddf
出典データセット
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04225527

反応ノート

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