Acetovanillone → 2',3'-Dihydroxyacetophenone

HRID 38631

反応式

HRID 38631 の反応式
[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]

参加物

5

反応物 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 64291102',3'-Dihydroxyacetophenone収率 70.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-904a19f9ad764a429ae73edd9fd181c0
出典データセット
uspto-grants-2013_09
特許番号
US08524740B2

関連ノート

読み込み中…