Carbon Dioxide → 4-Vinylphenol

HRID 1765955Notes

Reaction equation

HRID 1765955 reaction equation
C(O[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.[OH-].[K+].C1CCCCC1.ClCCl.C(=O)=[O:25]>O>[CH:6]([C:7]1[CH:12]=[CH:11][C:10]([OH:25])=[CH:9][CH:8]=1)=[CH2:5]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 1145762-Phenylvinyl acetate3×HCID 21916607Dichloromethane cyclohexane

Product 1

HCID 624534-Vinylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction is based on that described by Corson et al. J Org Chem (1958) 544–549; molar ratios acetoxystyrene:base 1:1.5. The base, KOH in water (30%) was immersed in an ice bath and the acetoxystyrene was added dropwise over 30 mins (all reaction carried under N2; the reaction was TLC monitored (20–80 cyclohexane-dichloromethane) until all acetoxystyrene disappeared, then the pH was brought down to 8 with CO2; the resulting precipitate was filtered and washed with water, then recrystallised from boiling hexane and NMR characterised.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customrecrystallised

Sources & evidence

ORD record
ord-4ecf5b0b53964816bafa471ff6f73896
Source dataset
uspto-grants-2007_06
Patent number
US07229836B2

Reaction notes

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