Hydrochloric Acid → HCID 14746282, compound

HRID 1089356Notes

Reaction equation

HRID 1089356 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.Cl>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 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 pH 2 and extracted twice with ether, the ether phase is washed twice with water and 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.) are obtained by recrystallization from petroleum ether.

Workup

  1. extractionextracted twice with ether
  2. washthe ether phase is washed twice with water
  3. dry with materialdried over sodium sulfate
  4. customthe ether is removed with a rotary evaporator at room temperature under aspirator vacuum
  5. customare obtained by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-341a78b099c54dc7ab672665b869b523
Source dataset
uspto-grants-1990_10
Patent number
US04965400

Reaction notes

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