Benzaldehyde → 3-Chloro-1-phenyl-3-buten-1-ol

HRID 256736Notes

Reaction equation

HRID 256736 reaction equation
[Cl:1][C:2]([CH2:4]Cl)=[CH2:3].[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>[Zn].C(O)(=O)C>[Cl:1][C:2](=[CH2:3])[CH2:4][CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:13]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 1140TolueneHCID 65652,3-Dichloropropene

Product 1

HCID 146636783-Chloro-1-phenyl-3-buten-1-olYield 95.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

125.40 Grams of 2,3-dichloro-1-propene were added dropwise to a mixture of 60.00 g of benzaldehyde, 180 g of toluene, 240 g of 5% acetic acid and 73.88 g of zinc powder at 45° C., and then 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 subjected to separation. The organic phase was washed with a 7% sodium carbonate aqueous solution and dried over sodium sulfate. The desiccant was filtered off, and then the toluene was distilled off under reduced pressure to give 98.23 g of 2-chloroallylphenylcarbinol. The results were as follows.

Workup

  1. customto react at the same temperature for 3 hours
  2. filtrationwere filtered off
  3. customthe resultant filtrate was subjected to separation
  4. washThe organic phase was washed with a 7% sodium carbonate aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-844ea650780e43d795ec8dfa4a3ab69f
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

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