Water → HCID 14746282, compound

HRID 1607959Notes

Reaction equation

HRID 1607959 reaction equation
C([O:4][C:5]1[C:12]([Br:13])=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][C:6]=1[Br:14])(=O)C.O.NN.O>C1COCC1.CO>[Br:13][C:12]1[CH:11]=[C:8]([CH:7]=[C:6]([Br:14])[C:5]=1[OH:4])[CH:9]=[CH2:10]

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 14746278HCID 14746278, compound

Product 1

HCID 14746282HCID 14746282, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g of 4-acetoxy-3,5-dibromostyrene are dissolved in 50 ml THF and 25 ml methanol, 12 g hydrazine hydrate (80% aqueous solution) is added, and the cloudy mixture is then converted into a clear solution by adding 3 ml of water. After 40 minutes it is acidified with a:semi-concentrated HCl to pH2 and extracted twice with ether the ether phase is washed twice with waterand dried over sodium sulfate and the ether is removed with a rotary evaporator at room temperature under aspirator vacuum. 8.5 g of crude product remain, from which 6.45 g of white crystals (mp 74° C.) areobtained by recrystallization from petroleum ether.

Workup

  1. extractionwith a:semi-concentrated HCl to pH2 and extracted twice with ether the ether phase
  2. washis washed twice with waterand
  3. dry with materialdried over sodium sulfate
  4. customthe ether is removed with a rotary evaporator at room temperature under aspirator vacuum
  5. customareobtained by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-2843d8b42f9840b48d9419fe992177e1
Source dataset
uspto-grants-1989_09
Patent number
US04868257

Reaction notes

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