Hydrochloric Acid → 2-(1-Hexenyl)phenol

HRID 1739479Notes

Reaction equation

HRID 1739479 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 542978452-(1-Hexenyl)phenolYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0ded745c870143968b1dc1553ffc5d00
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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