Sodium Hydroxide → HCID 20627927, compound

HRID 1924791Notes

Reaction equation

HRID 1924791 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([O:17]C)=[O:16])[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57458159HCID 57458159, compound

Product 1

HCID 20627927HCID 20627927, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 6-tert-butyl-2-naphthoate (843 mg, 3.48 mmol) and 2M sodium hydroxide solution (6.96 mmol, 3.48 mmol) in MeOH (30 ml) was heated at 60° C. for 3 hours. After cooling to ambient temperature, the solvent was evaporated in vacuo and the residue was acidified to pH 2 with 2M hydrochloric aqueous solution. The aqueous layer was extracted with EtOAc and the combined solution was washed with brine, dried over sodium sulfate and evaporated in vacuo to give the crude product which was recrystallized from EtOAc and hexane to furnish the title compound as a white solid (614 mg, 77%). 1H NMR (DMSO): δ 1.39 (9H, s), 7.70-7.76 (1H, m), 7.90-8.08 (4H, m), 8.55 (1H, br, s), 13.00 (1H, br, s).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was evaporated in vacuo
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas recrystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-e22523f3e4294256a4609e52bd10405c
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

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