Hydrochloric Acid → HCID 22404503, compound

HRID 259990Notes

Reaction equation

HRID 259990 reaction equation
[Br:1][C:2]([CH2:4]Br)=[CH2:3].[C:6]1([CH2:12][CH:13]=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>[Zn].C1(C)C=CC=CC=1>[Br:1][C:2]([CH2:4][CH:13]([OH:14])[CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 998PhenylacetaldehydeHCID 105522,3-Dibromopropene

Product 1

HCID 22404503HCID 22404503, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 1140TolueneSolvent

Procedure

49.93 Grams of 2,3-dibromo-1-propene were added dropwise to a mixture of 20.00 g of phenylacetaldehyde, 40 g of toluene, 60 g of 0.01% hydrochloric acid and 16.33 g of zinc powder at 30° C., and the mixture was allowed to react at the same temperature for 3 hours. After the reaction was completed, zinc-derived insolubles were filtered off, and the resultant filtrate was separated. The organic phase was washed with a 7% sodium carbonate aqueous solution, and the toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 24.01 g of 2-bromo-5-phenyl-1-penten-4-ol; nD25 =1.536, FI-MS m/e 240(M+), 242(M+2+).

Workup

  1. customto react at the same temperature for 3 hours
  2. filtrationwere filtered off
  3. customthe resultant filtrate was separated
  4. washThe organic phase was washed with a 7% sodium carbonate aqueous solution
  5. distillationthe toluene was distilled off under reduced pressure
  6. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d518e0a76f24831b5f38bb0f87b9b3e
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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