Chloroform → 2-Methoxy-7,8-dichloro-5,6,7,8-tetrahydronaphthalene-1,4-dione

HRID 726205

반응식

HRID 726205 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]2C[CH:7]=[CH:8][CH2:9][C:10]=2[C:11](=[O:13])[CH:12]=1.[Cl:15]Cl.CCOC(C)=O.COC1C(=O)C2C(C(=O)C=1)=CC=CC=2.[CH:37]([Cl:40])(Cl)Cl>CCO>[CH3:1][O:2][C:3]1[C:4](=[O:14])[C:5]2[CH:37]([Cl:40])[CH:7]([Cl:15])[CH2:8][CH2:9][C:10]=2[C:11](=[O:13])[CH:12]=1

참가 물질

7

반응물 5

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 168712-Methoxy-1,4-NaphthoquinoneHCID 24526ChlorineHCID 197105762-Methoxy-5,8-dihydronaphthalene-1,4-dione

생성물 1

HCID 197105382-Methoxy-7,8-dichloro-5,6,7,8-tetrahydronaphthalene-1,4-dione

시약·촉매·용매 1

HCID 702Ethanol용매3회

실험 절차

To a solution of 2-methoxy-5,8-dihydronaphthalene-1,4-dione (2.75 g, 14.4 mmol) in CHCl3 (60 mL, pre-treated with silica gel to remove the EtOH stabilizer) there was added a solution of Cl2 (~1.10 g, ~15.1 mmol) in EtOH-free CHCl3 (50 mL) in portions over 30 min. TLC (5% EtOAc/95% EtOH) indicated total consumption of the starting material and the appearance of a major higher Rf product spot (lower Rf impurity spots were also noted). The solvent was removed in vacuo to yield a yellow syrup. The addition of 95% EtOH (10 mL) followed by evaporation in vacuo (performed twice) yielded a yellow solid. Crystallization from 95% EtOH (dissolved in 20 mL, allowed to cool to rt) yielded a yellow solid (2.28 g, 60%, ~90% pure by TLC and 1H NMR, mp 119°-123° C.). Recrystallization from 95% EtOH (dissolved in 12 mL, allowed to cool to rt) yielded a yellow crystalline solid (1.89 g, 83% recovery, 50% total yield, ~95% pure by TLC and 1H NMR with the major impurity being 2-methoxynaphthalene-1,4-dione); mp 123°-128° C. (EtOH); 1H NMR (CDCl3) δ3.11 (m, 4H), 3.83 (s, 3H), 4.67 (m, 2H), 5.94 (s, 1H).

후처리

  1. customto remove the EtOH stabilizer) there
  2. customconsumption of the starting material
  3. customThe solvent was removed in vacuo
  4. customto yield a yellow syrup
  5. customfollowed by evaporation in vacuo (
  6. customyielded a yellow solid
  7. customCrystallization from 95% EtOH (dissolved in 20 mL, allowed to cool to rt)
  8. customyielded a yellow solid (2.28 g, 60%, ~90% pure by TLC and 1H NMR, mp 119°-123° C.)
  9. customRecrystallization from 95% EtOH (dissolved in 12 mL, allowed to cool to rt)
  10. customyielded a yellow crystalline solid (1.89 g, 83% recovery, 50% total yield, ~95% pure by TLC and 1H NMR with the major impurity

출처 및 근거

ORD 기록
ord-4179eb5938264de893d1c9c39a8d878b
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708168

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