Acetovanillone → 2',3'-Dihydroxyacetophenone

HRID 38631

반응식

HRID 38631 반응식
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9](O)=[C:6]([O:7]C)[CH:5]=1)=[O:3].C([O-])([O-])=[O:14].[K+].[K+].C(Br)C1C=CC=CC=1>CC#N>[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][CH:9]=[C:6]([OH:7])[C:5]=1[OH:14])=[O:3]

참가 물질

5

반응물 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

생성물 1

HCID 64291102',3'-Dihydroxyacetophenone수율 70.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
25 °C

실험 절차

To a solution of acetovanillone (33) (4.70 g, 28.3 mmol) in MeCN (60 mL) was added K2CO3 (8.05 g, 58.3 mmol) and KI (0.20 g, 1.2 mmol). The mixture was stirred under N2 atmosphere and benzyl bromide (34) (4.0 mL, 34 mmol) was added dropwise. The reaction mixture was reflux for 24 h and then cooled to 25° C., then resulting precipitate was filtered off. The filtrate was evaporated and purified by column chromatography (SiO2, n-hexane: CH2Cl2=1:2) to give 30. White solid; yield: 70.3%; mp 87-88° C.; 1H-NMR (CDCl3. 200 MHz): δ 2.51 (s, 3H), 3.91 (s, 3H), 5.20 (s, 2H), 6.86 (d, J=8.2 Hz, 1H), 7.21-7.55 (m, 7H); 13C-NMR (CDCl3, 50 MHz): δ 26.19, 56.05, 70.79, 110.53, 112.13, 123.07, 127.18, 128.10, 128.68, 130.72, 136.28, 149.49, 152.41, 196.80; Anal. calcd for C16H16O3: C, 74.98; H, 6.29. Found: C, 75.02; H, 6.25.

후처리

  1. temperatureThe reaction mixture was reflux for 24 h
  2. customresulting precipitate
  3. filtrationwas filtered off
  4. customThe filtrate was evaporated
  5. custompurified by column chromatography (SiO2, n-hexane: CH2Cl2=1:2)

출처 및 근거

ORD 기록
ord-904a19f9ad764a429ae73edd9fd181c0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524740B2

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