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Malonic Acid → 3-(4-Heptylphenyl)prop-2-enoyl chloride

HRID 460751
ノート
印刷プレビュー

反応式

HRID 460751 の反応式
C(C1C=CC(C=O)=CC=1)CCCCCC.C(O)(=O)CC(O)=O.[CH2:23]([C:30]1[CH:40]=[CH:39][C:33]([CH:34]=[CH:35][C:36](O)=[O:37])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].S(Cl)([Cl:43])=O>N1CCCCC1.CCOCC.N1C=CC=CC=1>[CH2:23]([C:30]1[CH:40]=[CH:39][C:33]([CH:34]=[CH:35][C:36]([Cl:43])=[O:37])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 867Malonic AcidHCID 24386Thionyl ChlorideHCID 109216344-HeptylbenzaldehydeHCID 53734772p-n-Heptylcinnamic acid

生成物 1

HCID 541980353-(4-Heptylphenyl)prop-2-enoyl chloride

試薬・触媒・溶媒 3

HCID 8082Piperidine触媒
HCID 1049
Pyridine
溶媒
HCID 3283Diethyl Ether溶媒

実験手順

8.8 G. of p-n-heptylbenzaldehyde and 8.74 g. of malonic acid are dissolved in 7 ml. of absolute pyridine, treated with 8 drops of piperidine and heated at 90°-100° C. for 68 hours. The mixture is then taken up in ether and washed with dilute hydrochloric acid. After recrystallization from ether/hexane, there are obtained 7.5 g. of p-n-heptylcinnamic acid having a melting point of 121°-122° C. and a clearing point of 150°-153° C. 8.2 G. of this acid are boiled at reflux in 120 ml. of thionyl chloride for 30 minutes. The excess thionyl chloride is removed by distillation, the residue taken up three times in absolute toluene, concentrated and dried. The p-n-heptylcinnamic acid chloride obtained can be used in the process directly.

後処理

  1. temperatureheated at 90°-100° C. for 68 hours
  2. washwashed with dilute hydrochloric acid
  3. customAfter recrystallization from ether/hexane, there
  4. customare obtained 7.5 g
  5. customa clearing point of 150°-153° C
  6. temperatureat reflux in 120 ml
  7. customThe excess thionyl chloride is removed by distillation
  8. concentrationconcentrated
  9. customdried

出典と根拠

ORDレコード
ord-5f90ec3a2e5b4aa7b1e6ba6e6613cfcf
出典データセット
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04061587

反応ノート

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