Benzenepropanal → HCID 9834042, compound

HRID 847582Notes

Reaction equation

HRID 847582 reaction equation
[CH:1]([Mg]Br)=[CH2:2].O1CCCC1.[CH:10](=[O:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[OH:19][CH:10]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 8028TetrahydrofuranHCID 178418507HCID 178418507, compound

Product 1

HCID 9834042HCID 9834042, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Vinylmagnesium Bromide (120 mmol, 1M) in ether was added to 80 ml of dry tetrahydrofuran and cooled under inert atmosphere to 0° C. Hydrocinnamaldehyde (8.0 ml, 61 mmol) was added dropwise, and the solution was stirred for 10 min, quenched cautiously with saturated aqueous ammonium chloride, extracted with ether, washed with saturated brine, dried over MgSO4, and concentrated to give 9.82 g (98.6%) of the crude desired product.

Workup

  1. customquenched cautiously with saturated aqueous ammonium chloride
  2. extractionextracted with ether
  3. washwashed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50d6decde34043188d932efd9bca1a71
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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