Hydrochloric Acid → 4-Benzyloxybenzonitrile

HRID 429761

反応式

HRID 429761 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CN(C=O)C.O.C(OCC)(=O)C>[CH2:16]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

生成物 1

HCID 5613714-Benzyloxybenzonitrile収率 93%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 4-cyanophenol (50 g, 0.42 mol) and potassium carbonate (150 g, 1.1 mol) in DMF (800 ml) was added benzyl bromide (75 ml, 0.63 mol). The reaction mixture was stirred for 2 h at room temperature before filtering off solid and reducing the filtrate in vacuo to give an oil. The solid precipitate was dissolved in water and the pH adjusted to 0.5 using 6.0M hydrochloric acid and extacted into ethyl acetate. The solvent was dried over magnesium sulphate and removed by evaporation in vacuo to give an oil. The two oil products were combined and triturated with diethyl ether/hexane to give a white solid, which was washed with hexane and dried to give the title compound (81 g, 93%). 1H NMR (CDCl3) δ 7.5 (2H, d, 1 8.6 Hz), 7.45-7.30 (5H, br m), 7.0 (2H, d, J 8.6 Hz) and 5.14 (2H, s). MS (ES) m/e 210 [M+H]+.

後処理

  1. filtrationbefore filtering off solid
  2. customto give an oil
  3. dry with materialThe solvent was dried over magnesium sulphate
  4. customremoved by evaporation in vacuo
  5. customto give an oil
  6. customtriturated with diethyl ether/hexane
  7. customto give a white solid, which
  8. washwas washed with hexane
  9. customdried

出典と根拠

ORDレコード
ord-26987c0b17784e589bc4bcd67eda28af
出典データセット
uspto-grants-2001_11
特許番号
US06319922B1

関連ノート

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