Sodium Hydroxide → HCID 59544179, compound

HRID 1094663Notes

Reaction equation

HRID 1094663 reaction equation
[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([C:15]([O:17]C)=[O:16])[CH:9]=[CH:8]3)[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8]3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66637193HCID 66637193, compound

Product 1

HCID 59544179HCID 59544179, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Methyl 6-(1-methylcyclopropyl)-2-naphthoate (crude 0.91 g, 2.5 mmol) and 2M sodium hydroxide solution (3.8 ml) in methanol (7.6 ml) was heated at 60° C. for 2 hours. After cooling to room temperature, the mixture was washed with diethyl ether (100 ml). The aqueous layer was acidified to pH<3 with 2M hydrochloric acid solution and the mixture was extracted with dichloromethane-methanol (10:1, 150 ml×3 times). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 0.444 g (78% yield for 2 steps) of the title compound as white solid. 1H NMR (300 MHz, DMSO-d6) ppm 0.77-0.92 (2H, m), 0.95-1.11 (2H, m), 1.49 (3H, s), 7.42 (1H, d, J=8.8 Hz), 7.84 (1H, s), 7.90-7.97 (2H, m), 8.01 (1H, d, J=8.8 Hz), 8.54 (1H, s). MS (ESI): m/z 225 (M−H)−.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with diethyl ether (100 ml)
  3. extractionthe mixture was extracted with dichloromethane-methanol (10:1, 150 ml×3 times)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a358088bc53a4ba58152dd711628a25a
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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