Ethylparaben → Ethyl4-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate

HRID 484373Notes

Reaction equation

HRID 484373 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.O[C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:24]([O:23][C:21](=[O:22])[C:20]1[CH:26]=[CH:27][C:17]([O:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]3[CH2:5][CH2:4][CH2:3][C:2]([CH3:15])([CH3:1])[C:11]=3[CH:10]=2)=[O:14])=[CH:18][CH:19]=1)[CH3:25]

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 10868DicyclohexylcarbodiimideHCID 197480028,8-Dimethyl-5,6,7,8-tetrahydro-2-naphthoic acid

Product 1

HCID 19748024Ethyl4-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 220.7 mg (1.0804 mmol) of 8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoic acid, 180.6 mg (1.0868 mmol) of ethyl 4-hydroxybenzoate, 227.3 mg (1.1034 mmol) of 1,3-dicyclohexylcarbodiimide and 22.9 mg (0.1874 mmol) of 4-dimethylaminopyridine in 15 ml of methylene chloride was stirred at room temperature for 18 h. The reaction mixture was then filtered and the residue washed with 10 ml of methylene chloride. The filtrate was concentrated in-vacuo and the resultant crude product purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.35 (6H, s), 1.42 (3H, t, J~7.2 Hz), 1.68-1.76 (2H, m), 1.80-1.92 (2H, m), 2.85 (2H, t, J~6.1 Hz), 4.40 (2H, q, J~7.2 Hz), 7.18 (1H, d, J~ 8.0 Hz), 7.31 (2H, d, J~8.7 Hz), 7.89 (1H, dd, J~8.0 Hz, 1.6 Hz), 8.11-8.22 (3H, m).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe residue washed with 10 ml of methylene chloride
  3. concentrationThe filtrate was concentrated in-vacuo
  4. customthe resultant crude product purified by flash chromatography (silica; 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9676058740634d2e87c91ed35b9267a7
Source dataset
uspto-grants-1993_07
Patent number
US05231113

Reaction notes

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