Hydrochloric Acid → [4-(1,3-Benzoxazol-2-yl)phenyl](2-hydroxy-4-methoxyphenyl)methanone

HRID 1288413노트

반응식

HRID 1288413 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.ClC(Cl)C.Cl>ClCCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=2[OH:31])=[O:15])=[CH:12][CH:11]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 90073-MethoxyphenolHCID 6451240Aluminum(III) ChlorideHCID 20556623HCID 20556623, 화합물

생성물 1

HCID 21501898[4-(1,3-Benzoxazol-2-yl)phenyl](2-hydroxy-4-methoxyphenyl)methanone수율 61%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
10 °C

실험 절차

To a stirred solution of 12.8 g. (0.05 mole) of 4-(2-benzoxazolyl)benzoyl chloride in 200 ml. of 1,2-dichloroethane is added, in small increments, 14.8 g. (0.11 mole) of anhydrous alumimum chloride at room temperature. The resulting solution is cooled to 10° C. and a solution of 6.2 g. (0.05 mole) of m-methoxyphenol in 50 ml. of dichloroethane is added dropwise over a period of 10 min. The reaction mixture is stirred at 10° C. for 30 min., then allowed to warm to room temperature and stirred at reflux for 1 hr. The reaction mixture is cooled to room temperature and combined with 300 g. cracked ice containing 50 ml. of concentrated hydrochloric acid. The organic layer is separated and washed 2 times with warm water. The organic layer is filtered through filter-cel and the solvent is evaporated on a steam bath leaving a yellow solid residue. The crude solid product is recrystallized from toluene to give 10 g. yellow crystals, m.p. 177°-179° C. (61% yield). The structure and purity of the product are confirmed by IR, NMR, and elemental analysis.

후처리

  1. customat room temperature
  2. temperatureto warm to room temperature
  3. stirringstirred
  4. temperatureat reflux for 1 hr
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customThe organic layer is separated
  7. washwashed 2 times with warm water
  8. filtrationThe organic layer is filtered
  9. filtrationthrough filter-cel
  10. customthe solvent is evaporated on a steam bath
  11. customleaving a yellow solid residue
  12. customThe crude solid product is recrystallized from toluene
  13. customto give 10 g

출처 및 근거

ORD 기록
ord-d27c7cf4f3bc4f81be949ddaf6f05fa7
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03988295

반응 노트

불러오는 중…