Ethyl Acetate → 5-(3-Phenoxypropoxy)indan-1,3-dione

HRID 1706464노트

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HRID 1706464 반응식
[O:1]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]([O:24]C)=O)[C:15](=[CH:20][CH:21]=1)[C:16]([O:18]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:28](OCC)(=O)C>CC(C)=O>[O:1]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:20][CH:21]=1)[C:16](=[O:18])[CH2:28][C:22]2=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 20331397Dimethyl 4-(3-phenoxypropoxy)phthalate

생성물 1

HCID 203313915-(3-Phenoxypropoxy)indan-1,3-dione수율 22%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of dimethyl 4-(3-phenoxypropoxy)phthalate (13.6 g., 0.0395 mole) in ethyl acetate (12 ml) was added to a 50% dispersion of sodium hydride in mineral oil (2.54 g) and the mixture heated at reflux for 4 hrs. After cooling, the mixture was triturated with 50% ethanol, ether and the yellow solid filtered off and added to a hot (70°-80° C.) 10% solution of hydrochloric acid (150 ml). After 2 mins a yellow oily solid separated which was isolated by decantation and taken up in acetone from which it crystallised on concentration to give 2.533 g (22%) of material of m.p. 91°-94° C., νmax (mull) 1740, 1710, 1605 cm-1 ; τ(DMSO) 7.78 (2H quintet; J 6.4 Hz); 6.68 (2H, s); 5.83 (2H, t, J 6.4 Hz); 5.62 (2H, t, J 6.4 Hz); 3.21- 2.44 (7H, m); 2.12 (1H, m). (Found; C, 72.97; H, 5.61; C18H16O4 requires; C, 72.96; H, 5.44%).

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hrs
  3. temperatureAfter cooling
  4. customthe mixture was triturated with 50% ethanol, ether
  5. filtrationthe yellow solid filtered off
  6. additionadded to a hot (70°-80° C.) 10% solution of hydrochloric acid (150 ml)
  7. customAfter 2 mins a yellow oily solid separated which
  8. customwas isolated by decantation
  9. customcrystallised on concentration

출처 및 근거

ORD 기록
ord-7280f1fd171a480281e2667f3385c788
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04207335

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