Sodium Hydroxide → 1,2,3,4-Tetrahydro-1-naphthaleneacetic acid

HRID 331223Notes

Reaction equation

HRID 331223 reaction equation
[CH:1]1([CH2:11][C:12]([O:14]CC)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12322859Ethyl (1,2,3,4-tetrahydronaphthalen-1-yl)acetate

Product 1

HCID 128585751,2,3,4-Tetrahydro-1-naphthaleneacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (1,2,3,4-tetrahydronaphthalen-1-yl)acetate (31.0 g) in ethanol (100 ml) was added sodium hydroxide (4N, 100 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated to a half volume under reduced pressure, and the residue was washed with ethyl acetate. The aqueous layer was acidified with dilute hydrochloric acid, and extracted with chloroform. The obtained organic layer was washed with water and saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure to give (1,2,3,4-tetrahydronaphthalen-1-yl)acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated to a half volume under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. extractionextracted with chloroform
  4. washThe obtained organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b4169e97d424a269bd33292661e084e
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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