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

HRID 1739483

反応式

HRID 1739483 の反応式
[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]

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 2724565Pentyltriphenylphosphonium bromideHCID 178418261HCID 178418261、化合物

生成物 1

HCID 538311814-(1-Hexenyl)phenol収率 85.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-41a8bfd3c65d40f98b729cab42e5078f
出典データセット
uspto-grants-1999_10
特許番号
US05965741

関連ノート

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