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

HRID 75145

반응식

HRID 75145 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-42ea015766b440f091058e5f05edbb7f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835426B2

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