Carbon Dioxide → 1,3-Dihydroxy-2-naphthoic acid methyl ester

HRID 488679Notes

Reaction equation

HRID 488679 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[C:13](=[O:16])(O)[O-:14].[K+].[C:18](=O)=O.Cl>OCC(CO)O>[CH3:18][O:14][C:13]([C:3]1[C:4]([OH:12])=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[OH:1])=[O:16]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 86011,3-DihydroxynaphthaleneHCID 516893Potassium Bicarbonate

Product 1

HCID 450935251,3-Dihydroxy-2-naphthoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

A mixture of 1,3-dihydroxynaphthalene (480 mg, 3.00 mmol) and potassium bicarbonate (750 mg, 7.5 mmol) in glycerol (1 mL) was heated under 1 atmosphere of CO2 to 115° C. for 5 hours then poured into 0.5M HCl (20 mL) and extracted with diethyl ether (3×5 mL). The combined ether layers were washed with brine (1×5 mL), dried (MgSO4) and filtered. This solution was then treated with a solution of diazomethane in diethyl ether until bubbling ceased. The ether was removed under reduced pressure and purified on silica gel eluting with 20% ethyl acetate/hexanes to provide (75 mg, 11%).

Workup

  1. extractionextracted with diethyl ether (3×5 mL)
  2. washThe combined ether layers were washed with brine (1×5 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. additionThis solution was then treated with a solution of diazomethane in diethyl ether
  6. customuntil bubbling
  7. customThe ether was removed under reduced pressure
  8. custompurified on silica gel eluting with 20% ethyl acetate/hexanes
  9. customto provide (75 mg, 11%)

Sources & evidence

ORD record
ord-29c698a687c448b69b0949fe5757c209
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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