Dimethyl Disulfide → 3-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde

HRID 1110819노트

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HRID 1110819 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[OH:10])[CH:5]=[O:6].[CH3:19][S:20]SC>[Cu].N1C=CC=CC=1>[CH3:19][S:20][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[OH:10])[CH:5]=[O:6]

참가 물질

5

반응물 2

HCID 12232Dimethyl DisulfideHCID 150782813-Bromo-4-hydroxy-5-benzyloxybenzaldehyde

생성물 1

HCID 117781083-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde수율 76%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 1049Pyridine용매

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온도
95 °C

실험 절차

In an alternative procedure a 50-L flask equipped with a mechanical stirrer was charged with 3-bromo-4-hydroxy-5-benzyloxybenzaldehyde (1.332 kg, 4.34 mol), Copper powder (1.068 kg, 16.82 mol), dimethyldisulfide (1.068 kg, 11.36 mol) and pyridine (23 L). The mixture was heated at 95° C. overnight with gentle stirring, filtered, and the filtered cake was washed with dichloromethane (30 L). The pyridine filtrate was distilled off to leave a black residue, from which the product was extracted with the dichloromethane washes. The combined organic extracts were washed with 2N HCl until it became light brown and the acidic aqueous layer was clear. The organic layer was dried (MgSO4), filtered, and the filtrate was evaporated to dryness. Crystallization from dichloromethane-hexane gave the title compound (900 g, 76%): mp 117°-119° C.; NMR (CDCl3) δ 2.50 (s, SCH3), 5.20 (s, OCH2Ar), 6.72 (s, OH), 7.34-7.46 (m, ArH), 9.78 (s, ArCHO)

후처리

  1. customIn an alternative procedure a 50-L flask equipped with a mechanical stirrer
  2. filtrationfiltered
  3. washthe filtered cake was washed with dichloromethane (30 L)
  4. distillationThe pyridine filtrate was distilled off
  5. customto leave a black residue
  6. extractionfrom which the product was extracted with the dichloromethane
  7. washThe combined organic extracts were washed with 2N HCl until it
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate was evaporated to dryness
  11. customCrystallization from dichloromethane-hexane

출처 및 근거

ORD 기록
ord-d55cb4eadbec4f4ca34f934e2b6b3dd5
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04977146

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