Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 34731

반응식

HRID 34731 반응식
[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]

참가 물질

8

반응물 4

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 8058HexaneHCID 24758Sodium hydride

생성물 1

HCID 4645407Methyl 4-(allyloxy)benzoate

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-884ac44b2889485ba15961c33b4cdcbb
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762921

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