Ethylparaben → Ethyl 4-[{(5,5-dimethyl-8-(phenylthio)-5,6-dihydronaphthalen-2-yl)carbonyl}oxy]benzoate

HRID 992138Notes

Reaction equation

HRID 992138 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[CH:7]=[C:6]([C:19]([OH:21])=[O:20])[CH:5]=[CH:4][C:3]1=2.O[C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1.Cl.CN(C)CCCN=C=NCC.CCOC(C)=O>CN(C=O)C>[CH3:1][C:2]1([CH3:22])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2[CH:7]=[C:6]([C:19]([O:21][C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)=[O:20])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225715435,5-Dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylic acid

Product 1

HCID 22571515Ethyl 4-[{(5,5-dimethyl-8-(phenylthio)-5,6-dihydronaphthalen-2-yl)carbonyl}oxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylic acid (Compound E19, 150.0 mg, 0.484 mmol), ethyl 4-hydroxybenzoate (88.5 mg, 0.530 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (120.6 mg, 0.630 mmol), and 4-N,N-dimethylaminopyridine (77.0 mg, 0.630 mmol) in 5.0 mL DMF was stirred overnight at room temperature. EtOAc (50 mL) was added and the solution washed with H2O and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure and column chromatography (10-15% EtOAc-hexanes) of the residual oil afforded the title compound as a colorless solid.

Workup

  1. washthe solution washed with H2O and saturated aqueous NaCl
  2. dry with materialbefore being dried over MgSO4
  3. customRemoval of the solvents under reduced pressure and column chromatography (10-15% EtOAc-hexanes) of the residual oil

Sources & evidence

ORD record
ord-02eef11c78cb4d68a8b35fb551c774f0
Source dataset
uspto-grants-2002_10
Patent number
US06465663B2

Reaction notes

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