3-Methylbenzaldehyde → m-Ethylbenzaldehyde

HRID 972974

반응식

HRID 972974 반응식
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[Br-].[C:11]([C:15]1[CH:40]=[CH:39][CH:38]=[CH:37][C:16]=1[CH2:17][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13]C)=[O:12].[CH3:41][C:42]1[CH:43]=[C:44]([CH:56]=[CH:57][CH:58]=1)[CH:45]=[CH:46]C1C(C(O)=O)=CC=CC=1>C(#N)C>[CH2:9]([C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[CH:7]=[O:8])[CH3:11].[CH2:45]([C:44]1[CH:43]=[C:42]([CH:58]=[CH:57][CH:56]=1)[CH:41]=[CH:17][C:16]1[C:15]([C:11]([OH:13])=[O:12])=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:46]

참가 물질

6

반응물 3

HCID 121053-MethylbenzaldehydeHCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideHCID 536852163'-Methylstilbene-2-carboxylic acid

생성물 2

HCID 118623m-EthylbenzaldehydeHCID 536634343'-Ethylstilbene-2-carboxylic acid

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

116.5 Gm. of 1,5-diazabicyclo[3.4.0]nonene-5 is added to 107.5 gm. of m-tolualdehyde and 400 gm. of o-carbomethoxybenzyltriphenylphosphonium bromide in 2000 ml. of acetonitrile. The mixture is refluxed briefly then cooled and the solvent removed under vacuum. The residue is dissolved in chloroform and washed with dilute hydrochloric acid, and the solution dried and evaporated. The product is refluxed for 11 hours in a solution of 111 gm. potassium hydroxide in 1000 ml. of water and 150 ml. of methanol. The solution is cooled and extracted with chloroform. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with chloroform. The extract is dried and evaporated to give 177.5 gm. (91%) of 3'-methylstilbene-2-carboxylic acid (ca. 60:40 cis:trans). Use of m-ethylbenzaldehyde instead of m-tolualdehyde gives a similar yield of 3'-ethylstilbene-2-carboxylic acid.

후처리

  1. temperatureThe mixture is refluxed briefly
  2. temperaturethen cooled
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with dilute hydrochloric acid
  6. customthe solution dried
  7. customevaporated
  8. temperatureThe product is refluxed for 11 hours in a solution of 111 gm
  9. temperatureThe solution is cooled
  10. extractionextracted with chloroform
  11. extractionextracted with chloroform
  12. customThe extract is dried
  13. customevaporated
  14. customto give 177.5 gm

출처 및 근거

ORD 기록
ord-d8bfa84b957d4c42a2ca510c1f885330
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04054579

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