Carbon Dioxide → HCID 13202154, compound

HRID 1734574Notes

Reaction equation

HRID 1734574 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH3:16])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.[C:17](=[O:19])=[O:18].Cl>CCCCCC.O1CCCC1>[CH3:15][O:14][C:12]1[CH:11]=[C:10]([CH3:16])[CH:9]=[C:8]([O:7][CH3:6])[C:13]=1[C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 778443,5-DimethoxytolueneHCID 178418339Butyllithium

Product 1

HCID 13202154HCID 13202154, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

104 ml of 1.6M n-butyllithium solution in hexane are added to 200 ml of tetrahydrofuran, followed by dropwise addition of 25 ml of 3,5-dimethoxytoluene, at a temperature between 0° and 5° C. The reaction medium is stirred at 5° C. for 1 h 30, followed by introduction of excess gaseous CO2 over 30 minutes. The mixture is introduced into 200 ml of aqueous 0.5N HCl solution and the aqueous phase is extracted with ethyl acetate. The residue is concentrated and chromatographied on a silica column (eluent: dichloromethane/methanol - 93/7).

Workup

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. concentrationThe residue is concentrated

Sources & evidence

ORD record
ord-464b2886669f4222b9b2479bc6a39820
Source dataset
uspto-grants-1996_07
Patent number
US05534530

Reaction notes

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