2,4-Dihydroxybenzaldehyde → 4-(4-Chloro-benzyloxy)-2-hydroxybenzaldehyde

HRID 2426125노트

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HRID 2426125 반응식
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F-].[K+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>C(#N)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:10][C:8]2[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=2)=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 72132,4-DihydroxybenzaldehydeHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 522689Potassium Fluoride

생성물 1

HCID 861018764-(4-Chloro-benzyloxy)-2-hydroxybenzaldehyde

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

A mixture of 2,4-dihydroxybenzaldehyde (6.62 g, 48 mmol, Fluka), potassium fluoride (5.57 g, 96 mmol, Aldrich) and 4-chlorobenzyl chloride (13.50 g, 84 mmol, Aldrich) in acetonitrile (50 mL) was heated at 90° C. for 24 hours. After cooling, the mixture was partitioned between ether (2×100 mL) and water (2×100 mL). Organic layers were washed with brine (100 mL), combined, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (Biotage 75S, hexanes, then hexanes-dichloromethane 1:1 as solvent) to give partial separation. Pure fractions of product were combined and concentrated and the residue crystallized from hexanes with traces of dichloromethane to give 4-(4-chloro-benzyloxy)-2-hydroxy-benzaldehyde as white crystals. (Yield 4.74 g). Mother liquor and impure fractions were combined and further purified by flash chromatography (Biotage 40L, same solvent as before) and pure fractions were combined and concentrated. The residue was re-crystallized to give second crop of 4-(4-chloro-benzyloxy)-2-hydroxy-benzaldehyde. (Yield 3.03 g).

후처리

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ether (2×100 mL) and water (2×100 mL)
  3. washOrganic layers were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (Biotage 75S, hexanes
  8. customhexanes-dichloromethane 1:1 as solvent) to give partial
  9. customseparation
  10. concentrationconcentrated
  11. customthe residue crystallized from hexanes with traces of dichloromethane

출처 및 근거

ORD 기록
ord-53198408ebea4c9f907dae617b068106
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968554B2

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