Sodium Hydroxide → HCID 22000899, compound

HRID 1787147Notes

Reaction equation

HRID 1787147 reaction equation
C([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([CH3:15])[CH:6]=1)(=O)C.[OH-].[Na+]>C1COCC1.CO>[CH3:15][C:7]1[CH:6]=[C:5]([OH:4])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22000894HCID 22000894, compound

Product 1

HCID 22000899HCID 22000899, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 3-methyl-5,6,7,8-tetrahydro-1-naphthalenyl acetate synthesized in Reference Example 173 (5.1 g, 25.1 mmol) in THF (120 mL) and methanol (30 mL) was added 12 N aqueous sodium hydroxide solution (2.5 mL) at room temperature, and the mixture was stirred for 30 minutes, and then concentrated under reduced pressure. Water and hydrochloric acid were added to the residue, and the mixture was acidified, which was extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was crystallized with ethyl acetate-hexane to obtain 4.1 g (yield 99%) of the title compound. Melting point: 95-96° C. (hexane-ethyl acetate).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and hydrochloric acid were added to the residue
  3. extractionwhich was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated brine, and then was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was crystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-f563f646f2b34ddcb36c6be94de3e454
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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