Phenylacetaldehyde → HCID 67027749, compound

HRID 1851180Notes

Reaction equation

HRID 1851180 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[CH:4][CH:3]=1.[C:13]1([CH2:19][CH:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-].C(OCC)(=O)C>C1COCC1>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([CH:20]([OH:21])[CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 6883421-Bromo-4-(dimethoxymethyl)benzene2×

Product 1

HCID 67027749HCID 67027749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of Mg turnings 2.4 g (0.1 mol) and 2 mL 1-bromo-4-(dimethoxymethyl)benzene (0.012 mol) in THF (100 mL) was heated under nitrogen atmosphere until the reaction starts. Subsequently additional 1-bromo-4-(dimethoxymethyl)benzene 14.71 mL (0.088 mol) dissolved in 30 mL THF was added slowly and the reaction refluxed for 1 h mixture to complete formation of the Gringnard reagent. A solution of 11.70 mL phenylacetaldehyde (0.1 mol) in 100 mL THF was added at to 0° C. and the reaction refluxed for 2 h upon completion of the addition. The mixture was worked up by pouring into saturated aqueous NH4Cl and extraction with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and the solvents were evaporated under reduced pressure. The brown-black oily product was used for the next step without purification.

Workup

  1. temperaturewas heated under nitrogen atmosphere until the reaction
  2. additionwas added slowly
  3. temperaturethe reaction refluxed for 1 h mixture to complete formation of the Gringnard reagent
  4. temperaturethe reaction refluxed for 2 h upon completion of the addition
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvents were evaporated under reduced pressure
  8. customThe brown-black oily product was used for the next step without purification

Sources & evidence

ORD record
ord-eaae717bac734cc9b42a1ce7b7b3bb0e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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