Water → 2-Naphthoic acid

HRID 249063Notes

Reaction equation

HRID 249063 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([O:15]C)=[O:14])[CH:7]=[CH:6]2.O>C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 5462224Magnesium

Product 1

HCID 71232-Naphthoic acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

33.3 g (79 mmol) of the compound produced in part (a) above, dissolved in 200 ml of THF are slowly added to a suspension of magnesium (2.9 g, 118 Atg) in 60 ml of THF. Once the addition is complete, the mixture is heated at reflux for 2 hours at which point the temperature of the mixture is permitted to return to ambient temperature. 10.8 g (79 mmol) of anhydrous zinc chloride are added and the mixture is stirred for one hour at ambient temperature, at which point 10.5 g (39.5 mmol) of methyl 6-bromo-2-naphthoate and 500 mg of NiCl2 /DPPE complex are added. This mixture is then stirred for 2 hours at ambient temperature, poured into water, extracted with CH2Cl2, dried and evaporated. The residue is chromatographed on a silica column (eluant: mixture of heptane (70%) and ether (30%). 18.5 (90%) of the methyl ester of 6-[3-(1-adamantyl)-4 ™tert.butyldimethylsilyloxyphenyl]-2-naphthoic acid are obtained. Melting point: 152°-153° C.

Workup

  1. additionOnce the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 2 hours at which point the temperature of the mixture
  4. customto return to ambient temperature
  5. additionare added
  6. extractionextracted with CH2Cl2
  7. customdried
  8. customevaporated
  9. customThe residue is chromatographed on a silica column (eluant
  10. additionmixture of heptane (70%) and ether (30%)

Sources & evidence

ORD record
ord-cb7167b7d03d4500b548a15d58a6f8d8
Source dataset
uspto-grants-1993_05
Patent number
US05212303

Reaction notes

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