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

HRID 460751
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HRID 460751 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 8082Piperidine촉매
HCID 1049
Pyridine
용매
HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f90ec3a2e5b4aa7b1e6ba6e6613cfcf
출처 데이터셋
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04061587

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