4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 75145

反応式

HRID 75145 の反応式
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[I-].[K+].CN([CH:21]=[O:22])C>CCOC(C)=O.O>[CH2:6]([O:22][C:21]1[CH:8]=[CH:9][C:2]([CH:10]=[O:13])=[CH:3][CH:4]=1)[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium Carbonate

生成物 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred mixture of 4-hydroxybenzaldehyde (28.2 g, 231 mmol), potassium carbonate (47.9 g, 35 mmol), potassium iodide and DMF(280 mL) benzyl bromide was added slowly at 0° C. The mixture was stirred at rt overnight. The mixture was diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with 1N aq HCl and dried. The solution was concentrated to give 4-benzyloxybenzaldehyde (46.5 g, 95%). 1H NMR: (CDCl3, 400 MHZ) δ=5.15 (s, 2H), 7.06 (m, 2H), 7.42(m, 5H), 7.84(m, 2H), 9.89(s, 1H).

後処理

  1. additionwas added slowly at 0° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with 1N aq HCl
  5. customdried
  6. concentrationThe solution was concentrated

出典と根拠

ORDレコード
ord-42ea015766b440f091058e5f05edbb7f
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

関連ノート

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