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

HRID 2105627Notes

Reaction equation

HRID 2105627 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-3901b4e348c641a5bf38e6cea7aebac5
Source dataset
uspto-grants-2009_08
Patent number
US07579372B2

Reaction notes

Loading…