Carbon Dioxide → HCID 18788310, compound

HRID 1106449Notes

Reaction equation

HRID 1106449 reaction equation
[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[CH:6][C:5]=1[O:14][CH3:15])[CH2:2][CH3:3].[Li]CCCC.[C:21](=[O:23])=[O:22].O>C1COCC1.CCCCCC>[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[C:8]([C:7]([O:12][CH3:13])=[CH:6][C:5]=1[O:14][CH3:15])[C:21]([OH:23])=[O:22])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 160945191,3,5-Trimethoxy-2-propylbenzeneHCID 178418339Butyllithium

Product 1

HCID 18788310HCID 18788310, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To the stirred solution of 2-propyl-1,3,5-trimethoxybenzene (3.00 g, 14.27 mmol) in dry THF (50 mL) at 0° C. in nitrogen atmosphere was added 6.28 mL (15.7 mmol) of 2.5 M n-BuLi in hexane dropwise via syringe. After the resulting solution was stirred at room temperature for 4 hr, 20 g of dry ice was added in portions over 20 min. After 30 min 50 mL of water was added. The mixture was evaporated under reduced pressure to remove THF and the aqueous phase was extracted with ether, acidified with hydrochloric acid to pH 3, and extracted again with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated. Purification of the solid residue by flash chromatography on silica column with 10% MeOH in dichloromethane provided 1.67 g of the title compound: mp 129.0-130.0° C. dec; 1H NMR (CDCl3): 6.30 (1 H, s), 3.93 (3 H, s), 3.87 (3 H, s), 3.83 (3 H, s), 2.54 (2 H, m), 1.49 (2 H, sex, J=7.5 Hz), 0.94 (3 H, t, J=7.5 Hz).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto remove THF
  3. extractionthe aqueous phase was extracted with ether
  4. extractionextracted again with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification of the solid residue by flash chromatography on silica column with 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-b5aa7f13c0614020b17e81cb8f31f3ae
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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