Sodium Hydroxide → 2-(1-Naphthylmethyl)-6-phenylhexanoic acid

HRID 1607385Notes

Reaction equation

HRID 1607385 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.[OH-].[Na+]>C(O)C>[C:17]1([CH2:16][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]([OH:27])=[O:3])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13727090HCID 13727090, compound

Product 1

HCID 137270912-(1-Naphthylmethyl)-6-phenylhexanoic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.05 g of 2-(1-naphthylmethyl)-6-phenylhexanoic acid ethyl ester in 30 ml of ethanol was added 10 ml of a 2N-aqueous sodium hydroxide solution. The mixture was heated under reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added water, and the mixture was washed with diethyl ether to remove neutral materials. Then, the aqueous layer was acidified by adding concentrated hydrochloric acid. The solution was extracted with diethyl ether, and the ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.85 g of 2-(1-naphthylmethyl)-6-phenylhexanoic acid as a colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the residue was added water
  5. washthe mixture was washed with diethyl ether
  6. customto remove neutral materials
  7. additionby adding concentrated hydrochloric acid
  8. extractionThe solution was extracted with diethyl ether
  9. washthe ethereal layer was washed with a saturated sodium chloride aqueous solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c446f398c0e04b2ab4bb61106c6cc525
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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