p-Toluenesulfonic acid → Ethyl 2-naphthylacetate

HRID 993073Notes

Reaction equation

HRID 993073 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=[O:13].[C:15]1(C)C=CC(S(O)(=O)=O)=C[CH:16]=1>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 113932-Naphthaleneacetic acid

Product 1

HCID 256821Ethyl 2-naphthylacetateYield 906.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-naphtylacetic acid (5 g) in 50 ml of ethanol are added 0.5 g of paratoluensulfonic acid, then the reaction mixture is refluxed for about 4 hours. The solvent is evaporated off and the residue is dissolved in diethyl ether, washed twice with a saturated aqueous solution of sodium hydrogencarbonate and once with brine, then the pooled organic extracts are dried over sodium sulfate and concentrated to dryness. 5.64 g of the product as a yellow oil are obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for about 4 hours
  2. customThe solvent is evaporated off
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washwashed twice with a saturated aqueous solution of sodium hydrogencarbonate and once with brine
  5. dry with materialthe pooled organic extracts are dried over sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-932c10e98151400facc7810be83e786d
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

Loading…