Dicyclohexylcarbodiimide → Methyl 2-hydroxy-1-naphthoate

HRID 430036

Reaction equation

HRID 430036 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[C:27]([OH:29])=[O:28]>CO>[OH:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[C:27]([O:29][CH3:1])=[O:28]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 167902-Hydroxy-1-naphthoic acid

Product 1

HCID 598533Methyl 2-hydroxy-1-naphthoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dicyclohexyicarbodiimide (1.20 Kg, 5.8 mol, 1.1 eq) was added portionwise over 4.5 hours to a cooled, mechanically-stirred slurry of 2-hydroxy-1-naphthoic acid (1.00 Kg, 5.3 mol) in methanol (3 L) under nitrogen. The internal temperature was maintained between 10 and 15° C. during the addition. Once the addition was complete, the mixture was allowed to warm to ambient temperature and stirred for 16 hours. The methanol was removed under reduced pressure and the residue taken up in ethyl acetate (5 L) and heated with stirring to 64° C. (internal temperature) and then allowed to cool once again to ambient temperature. The mixture was filtered, and the solid washed with ethyl acetate (0.7 L). The ethyl acetate solutions were combined and concentrated under reduced pressure. The residue (2.5 Kg) was recrystallised from ethanol-water (9:1, 3.3 L) and dried under vacuum at ambient temperature. Yield 0.92 Kg, 85%

Workup

  1. temperatureThe internal temperature was maintained between 10 and 15° C. during the addition
  2. additionOnce the addition
  3. customThe methanol was removed under reduced pressure
  4. temperatureheated
  5. stirringwith stirring to 64° C. (internal temperature)
  6. temperatureto cool once again to ambient temperature
  7. filtrationThe mixture was filtered
  8. washthe solid washed with ethyl acetate (0.7 L)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue (2.5 Kg) was recrystallised from ethanol-water (9:1, 3.3 L)
  11. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-3c9293eecaa740f3bf21a31028b3c5a5
Source dataset
uspto-grants-2001_11
Patent number
US06320068B1

Linked notes

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