Bromine → 1,1,3,4,4,6-Hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene

HRID 1579075

반응식

HRID 1579075 반응식
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH3:13])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH:4]([CH3:18])[CH2:3]1.[Br:20]Br>C(O)(=O)C>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH2:13][Br:20])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH:4]([CH3:18])[CH2:3]1

참가 물질

4

반응물 2

HCID 24408BromineHCID 89440Tonalide

생성물 1

HCID 214306251,1,3,4,4,6-Hexamethyl-7-bromacetyl-1,2,3,4-tetrahydronaphthalene수율 38%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

1,1,3,4,4,6-Hexamethyl-7-acetyl-1,2,3,4-tetrahydronaphthalene (33 gm,0.12 m) was dissolved in glacial acetic acid (40 ml.) and the solution treated portionwise with bromine (20.3 gm) with stirring. The mixture was allowed to stand overnight at room temperature and poured onto ice (100 gm.). The resulting mixture was extracted with ether (3 ×100 ml.) and the combined extracts washed with saturated sodium carbonate (2 × 50 ml.) and then brine. The washed extracts were then dried (MgSO4) and the solvent removed in vacuo to give a crystalline solid. This was recrystallised from absolute ethanol to give 1,1,3,4,4,6-hexamethyl-7-bromoacetyl-1,2,3,4-tetrahydronaphthalene as colourless needles (16 gm, 38%) m.p. 68°C. [Found: C, 64.40; H, 7.65%. C18H25BrO requires: C,64.09; H,7.47%].

후처리

  1. additionpoured onto ice (100 gm.)
  2. extractionThe resulting mixture was extracted with ether (3 ×100 ml.)
  3. washthe combined extracts washed with saturated sodium carbonate (2 × 50 ml.)
  4. dry with materialThe washed extracts were then dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a crystalline solid
  7. customThis was recrystallised from absolute ethanol

출처 및 근거

ORD 기록
ord-4f836ff607a94dd1952b1bc909ba4724
출처 데이터셋
uspto-grants-1976_02
특허 번호
US03940443

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