Carbon Dioxide → HCID 57602488, compound

HRID 1787942Notes

Reaction equation

HRID 1787942 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:11][CH:12]=2)[O:6][CH2:5][CH2:4][O:3]1.C([Li])(C)(C)C.[C:22](=[O:24])=[O:23]>CCOCC>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([C:22]([OH:24])=[O:23])=[C:9]([O:13][CH2:14][O:15][CH3:16])[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 57602458HCID 57602458, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 57602488HCID 57602488, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of methoxymethyl 3-(2-methyl-1,3-dioxolan-2-yl)phenyl ether (8.16 g, 36.4 mmol) in ether (200 mL) was added dropwise tert-butyl lithium (1.7 M solution, 26.8 mL, 1.25 equivalents) at −5 to −10° C. The reaction mixture was stirred 15 min before carbon dioxide gas was bubbled in for 5 min. The reaction mixture was allowed to warm slowly in the cold bath to about 10° C., then it was extracted with water. The aqueous layer was acidified with 5 N HCl and extracted with EtOAc. The organic phase was dried (MgSO4) and evaporated to afford a crude product which was triturated with hexane to afford the benzoic acid (4.54 g).

Workup

  1. customwas bubbled in for 5 min
  2. extractionit was extracted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customto afford a crude product which
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-7fdc48bc0b414ef59a18e4908777305b
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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