4-Hydroxybenzaldehyde → 4-(1-Hexenyl)phenol

HRID 1739483Notes

Reaction equation

HRID 1739483 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.[OH:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=1>C1COCC1>[CH:41]([C:40]1[CH:43]=[CH:44][C:37]([OH:36])=[CH:38][CH:39]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 2724565Pentyltriphenylphosphonium bromideHCID 178418261HCID 178418261, compound

Product 1

HCID 538311814-(1-Hexenyl)phenolYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of pentyl triphenylphosphonium bromide (4.76 g, 11.5 mMol) in freshly distilled THF (40 ml) was added LiN(SiMe3)2 (1N in THF, 23 ml). The red solution was stirred at ambient temperature for 30 minutes then a solution of p-hydroxybenzaldehyde (1.06 g, 10 mMol) in THF (10 ml) added. The reaction was stirred at ambient temperature for 4 days, then partitioned between ethyl ether and dilute aqueous HCl (1N). The combined etherial extracts were washed with brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography (eluant: ethyl ether/hexane) to give 4-(1-hexenyl)phenol as a pale yellow solid (1.5 g, 85%).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 4 days
  2. custompartitioned between ethyl ether and dilute aqueous HCl (1N)
  3. washThe combined etherial extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude oil was purified by chromatography (eluant: ethyl ether/hexane)

Sources & evidence

ORD record
ord-41a8bfd3c65d40f98b729cab42e5078f
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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