2,4-Dihydroxybenzaldehyde → HCID 10537643, 화합물

HRID 322948노트

반응식

HRID 322948 반응식
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

5

반응물 3

HCID 72132,4-DihydroxybenzaldehydeHCID 24758Sodium hydrideHCID 124874623-(Chloromethyl)thiophene

생성물 1

HCID 10537643HCID 10537643, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A solution of 2,4-dihydroxybenzaldehyde (42.6 g) in dimethylformamide (250 mL) at ambient temperature is treated with sodium hydride (13.5 g; 60% w/v dispersion in mineral oil; 338 mmol), portionwise during 30 minutes. It is then treated with 3-chloromethylthiophene and the reaction mixture is heated at 60° C. for 3 hours. The mixture is concentrated in vacuo and the residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent is removed in vacuo. Flash chromatography on silica gel, using a mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent, gives 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (11.8 g), in the form of a white solid.

후처리

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic extracts are washed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. additiona mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent

출처 및 근거

ORD 기록
ord-c8c18f4c75874b1a910d5d856be4a462
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211234B1

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