Ammonium Chloride → Benzenemethanol, alpha-1-propen-1-yl-

HRID 970770Notes

Reaction equation

HRID 970770 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9](=[O:13])/[CH:10]=[CH:11]/[CH3:12].[Cl-].[NH4+]>O1CCCC1.CCOCC>[C:1]1([CH:9]([OH:13])[CH:10]=[CH:11][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 447466CrotonaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 219674Benzenemethanol, alpha-1-propen-1-yl-Yield 99.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0–55° C.) 927 mL of 1 M solution of phenyl magnesium bromide in tetrahydofuran was added dropwise a solution of crotonaldehyde (65.0 g) in 130 mL of anhydrous ether over a period of 2 hours and 45 minutes. The reaction was stirred for an additional 45 minutes and then warmed to room temperature. After four more hours of stirring, saturated ammonium chloride aqueous solution (750 mL) was added to the reaction. The mixture was extracted with 750 mL of ether twice. The combined extract was dried over anhydrous potassium carbonate and filtered. The solvent was evaporated to give 135.88 g (99.9%) of the desired 1-phenyl-2-buten-1-ol as an oil which was used in the next step without further purification.

Workup

  1. custom45 minutes
  2. stirringAfter four more hours of stirring
  3. extractionThe mixture was extracted with 750 mL of ether twice
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cd38c19d795b4cf8bea6477f56979ecb
Source dataset
uspto-grants-2007_12
Patent number
US07312247B2

Reaction notes

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