Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 34731

反応式

HRID 34731 の反応式
[H-].[Na+].[CH3:3][CH2:4][CH2:5]CCC.[OH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(Br)C=C>CCOCC.O.CN(C=O)C>[CH2:5]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)[CH:4]=[CH2:3]

参加物

8

反応物 4

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 8058HexaneHCID 24758Sodium hydride

生成物 1

HCID 4645407Methyl 4-(allyloxy)benzoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

NaH (60% in oil, 10 g., 0.25 mol) was washed 3×100 ml. hexane in place. 350 ml. DMF was then added, the mixture stirred under N2, and methyl 4-hydroxybenzoate (38.0 g., 0.25 mol) added portionwise over 20 minutes as H2 evolved. Allyl bromide (21.6 ml., 0.25 mol) was then added via syringe over 5 minutes. After 40 minutes additional stirring, the reaction mixture was poured into 400 ml. ice and water and 150 ml. ether was added. The layers were separated and the aqueous layer extracted 4×150 ml. fresh ether and 1×100 ml. hexane. The organic layers were combined, washed 2×150 ml. saturated NaHCO3, dried over MgSO4, and stripped to yield title product, 47.6 g., 3.89 (s, 3H), 4.60 (m, 2H), 5.46 (m, 2H), 6.1 (m, 1H), 6.99 (d, 2 H), 8.10 (d, 2H).

後処理

  1. additionthe reaction mixture was poured into 400 ml
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted 4×150 ml
  4. washwashed 2×150 ml
  5. dry with materialsaturated NaHCO3, dried over MgSO4

出典と根拠

ORDレコード
ord-884ac44b2889485ba15961c33b4cdcbb
出典データセット
uspto-grants-1988_08
特許番号
US04762921

関連ノート

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