Hydrochloric Acid → 2-(1-Hexenyl)phenol

HRID 1739479

반응식

HRID 1739479 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH:36](=O)[C:37]1[C:38](=[CH:40][CH:41]=[CH:42][CH:43]=1)[OH:39].Cl>O.C1COCC1>[CH:36]([C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[OH:39])=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 2724565Pentyltriphenylphosphonium bromideHCID 178418261HCID 178418261, 화합물

생성물 1

HCID 542978452-(1-Hexenyl)phenol수율 88.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of pentyl triphenylphosphonium bromide (10.4 g, 25.2 mM) in freshly distilled THF (40 ml) was added LiN(SiMe3)2 (1M in THF, 50 ml). The reaction was stirred at ambient temperature for 1 hour. Salicylaldehyde (2.8 g, 22.9 mM) was added to the reaction mixture which was stirred at ambient temperature for 60 hours. The reaction was then treated with water, the pH adjusted with 1N aqueous HCl to pH7 and extracted twice with ethyl acetate. The organic layers were combined, dried over (MgSO4) and evaporated. The residue was purified by chromatography to give 2-(1-hexenyl)phenol, (3.57 g, 88%).

후처리

  1. stirringwas stirred at ambient temperature for 60 hours
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-0ded745c870143968b1dc1553ffc5d00
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965741

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