Carbon Dioxide → 6-Hydroxy-2-naphthoic acid

HRID 725696Notes

Reaction equation

HRID 725696 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[Li]CCCC.[C:18](=[O:20])=[O:19]>CCOCC>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:18]([OH:20])=[O:19])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 271446-Bromo-2-naphthalenolHCID 178418339Butyllithium

Product 1

HCID 855576-Hydroxy-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 500 mL three-neck flask fitted with magnetic stirrer, nitrogen lines and a 125 mL addition funnel was charged with 200 mL of dry ether (newly opened can) and 6-bromo-2-naphthol (15.6 g, 70 mmol). The atmosphere was replaced with nitrogen and a solution of 15 mL of 10M n-BuLi in 100 mL of ether (150 mmol) was added via the addition funnel over a 30 minute period. The solution became pale yellow with a precipitate. After stirring for 20 minutes more, dry ice was added until the solution became quite cold (<-25° C.) and green in color. The solution was warmed to room temperature and quenched by the addition of 200 mL of water. The two-phase system was transferred to a separatory funnel, the layers separated and the ether solution extracted with 100 mL of saturated NaHCO3 solution. The combined aqueous layers were washed with 100 mL of ether and neutralized by careful addition of 12N HCl. The pale blue solid was filtered and dried in the air to give 10.3 g (76%): mp 238-241° C. (dec.); lit. mp 240°-241° C.; reference: S. V. Sunthankar and H. Gilman, J. Org. Chem., 16, 8 (1951). ##STR26##

Workup

  1. customA 500 mL three-neck flask fitted with magnetic stirrer
  2. additionnitrogen lines and a 125 mL addition funnel
  3. custom(<-25° C.)
  4. customquenched by the addition of 200 mL of water
  5. customThe two-phase system was transferred to a separatory funnel
  6. customthe layers separated
  7. extractionthe ether solution extracted with 100 mL of saturated NaHCO3 solution
  8. washThe combined aqueous layers were washed with 100 mL of ether and neutralized by careful addition of 12N HCl
  9. filtrationThe pale blue solid was filtered
  10. customdried in the air
  11. customto give 10.3 g (76%)

Sources & evidence

ORD record
ord-9c48e57e88df4a20bcef4d17ff27aab1
Source dataset
uspto-grants-1998_01
Patent number
US05707559

Reaction notes

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