Iodine → Ethyl 3-phenylindan-1-acetate

HRID 1389823

反応式

HRID 1389823 の反応式
C1(C2C3C(=CC=CC=3)C(=O)C2)C=CC=CC=1.II.BrCC(OCC)=O.[C:26]1([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:33]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC=CC=1.[Zn].[Pd].C(O)(=O)C.CCOCC.O>[C:26]1([CH:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:33]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

11

反応物 4

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 981461-Indanone, 3-phenyl-HCID 54109097Ethyl 3-phenylindene-1-acetate

生成物 1

HCID 12565675Ethyl 3-phenylindan-1-acetate

試薬・触媒・溶媒 6

HCID 23938Palladium触媒HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

3-Phenyl-1-indanone (83 g, 0.4 mol) was dried by refluxing in C6H6 (120 ml) with removal of the azeotroped H2O. To this solution was added Et2O (120 ml) and Zn wool (26.25 g, 0.4 mol). The reaction mixture was heated to near reflux and a crystal of I2 added. Ethyl bromoacetate (110 g, 0.6 mol) was added over 2 hours, the temperature being kept near reflux by heat of reaction and some external heating. After the addition, the mixture was stirred and refluxed for a further 0.5 hour, cooled and poured into ice and acetic acid. The mixture was extracted with Et2O. The Et2O was washed with 1% NH4OH, dried (Na2SO4), filtered and evaporated and the residue distilled to give a mixture of ethyl 3-phenylindene-1-acetate and its corresponding double bond isomer (83.6g) b.p. 145°-155° C. (0.1 mm). This mixture of esters was hydrogenated over 10% Pd/C (0.6g) to give ethyl 3-phenylindan-1-acetate. This ester was hydrolyzed by refluxing with sodium hydroxide in ethanol to give the title compound, m.p. 126°-9° C.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto near reflux
  3. temperaturenear reflux
  4. temperatureby heat of reaction
  5. additionAfter the addition
  6. temperaturerefluxed for a further 0.5 hour
  7. temperaturecooled
  8. extractionThe mixture was extracted with Et2O
  9. washThe Et2O was washed with 1% NH4OH
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. distillationthe residue distilled
  14. customto give

出典と根拠

ORDレコード
ord-b553652ec8cd4a7f92aa2e1788d0cce0
出典データセット
uspto-grants-1981_01
特許番号
US04246281

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