Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 653030Notes

Reaction equation

HRID 653030 reaction equation
[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]

Participants

8

Reactant 4

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 8058HexaneHCID 24758Sodium hydride

Product 1

HCID 4645407Methyl 4-(allyloxy)benzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d59b0620355b4184a3ed2638ed1d1d2a
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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