Phenylacetaldehyde → HCID 11829757, compound

HRID 1429395Notes

Reaction equation

HRID 1429395 reaction equation
[C:1]1([CH2:7][CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][CH:12]=[CH2:13].Cl[Sn]Cl.O.CC(=O)OCC>O>[C:1]1([CH2:7][CH:8]([OH:9])[CH2:13][CH:12]=[CH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 43835034Tin dichloride dihydrate

Product 1

HCID 11829757HCID 11829757, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of phenylacetaldehyde 30a (7.84 g, 65.3 mmol) and 3-bromoprop-1-ene (11.1 g, 91.5 mmol) in water (50 mL), KI (3.25 g, 19.6 mmol) and NiCl2.6H2O (3.1 g, 13 mmol) were added. After the mixture was stirred for several minutes, SnCl2.H2O (29.5 g, 13 mmol) was added. The mixture was vigorously stirred at rt overnight and then extracted with EA. The combined organic layer was washed by brine, dried over anhydrous sodium sulfate, evaporated in vacuo. The residue was purified by CC using PE:EA=5:1 as mobile phase to give the desired product (5.75 g, 54% yield).

Workup

  1. additionwere added
  2. stirringThe mixture was vigorously stirred at rt overnight
  3. extractionextracted with EA
  4. washThe combined organic layer was washed by brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by CC

Sources & evidence

ORD record
ord-1d96dad93f5940288b2224e999ef6228
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…