Hydrochloric Acid → 4-Phenylbut-3-en-2-ol

HRID 1350604Notes

Reaction equation

HRID 1350604 reaction equation
[C:1]1([CH:7](O)[CH:8]=[CH:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CC[O:15]CC.C(=O)(O)[O-].[Na+]>O1CCOCC1>[C:1]1([CH:7]=[CH:8][CH:9]([OH:15])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 219674Benzenemethanol, alpha-1-propen-1-yl-HCID 516892Sodium Bicarbonate

Product 1

HCID 151724-Phenylbut-3-en-2-olYield 96.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Phenyl-2-buten-1-ol (135.88 g) was dissolved in 2300 mL of dioxane and treated with 2750 mL of dilute hydrochloric acid (2.3 mL of concentrated hydrochloric acid in 2750 mL of water) at room temperature. The mixture was stirred overnight and then poured into 4333 mL of ether and neutralized with 2265 mL of saturated aqueous sodium bicarbonate. The aqueous phase was extracted with 1970 mL of ether. The combined extract was dried over anhydrous potassium carbonate. Evaporation of the solvent followed by Kugelrohr distillation at 30° C. for 30 minutes afforded 131.73 g (96.8%) of the desired 4-phenyl-3-buten-2-ol as an oil which was used in the next step without further purification.

Workup

  1. extractionThe aqueous phase was extracted with 1970 mL of ether
  2. extractionThe combined extract
  3. dry with materialwas dried over anhydrous potassium carbonate
  4. customEvaporation of the solvent
  5. distillationfollowed by Kugelrohr distillation at 30° C. for 30 minutes

Sources & evidence

ORD record
ord-711642e6ae2f4b168d3b19dfefdbaca1
Source dataset
uspto-grants-2007_05
Patent number
US07214831B2

Reaction notes

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