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

HRID 1176110Notes

Reaction equation

HRID 1176110 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-81d5c10ecdcb4f7d833dfe4f0a0604d7
Source dataset
uspto-grants-2010_11
Patent number
US07842727B2

Reaction notes

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