Benzyl 4-Hydroxybenzoate → HCID 17949444, compound

HRID 394914Notes

Reaction equation

HRID 394914 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2.[CH2:24]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:24]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36]([O:16][C:15](=[O:17])[CH:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:23])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=3[CH:7]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:35][CH:34]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 10868DicyclohexylcarbodiimideHCID 17949413HCID 17949413, compound

Product 1

HCID 17949444HCID 17949444, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

300 mg of 2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-heptanoic acid were dissolved in 10 ml of methylene chloride and to this solution, were added successively, 240 mg of benzyl-4-hydroxybenzoate and 116 mg of N,N-dimethylaminopyridine. The reaction mixture was cooled to 0° C. and 217 mg of 1,3-dicyclohexylcarbodiimide was added at once. The mixture was stirred at 0° C. for 2 hours then at room temperature for 2 hours. The reaction mixture was filtered and the resulting filtrate was washed with 2 portions of 25 ml of water. The organic phase was dried over MgSO4 and the solvent evaporated. The oil/solid residue was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes) and gave 403 mg of a colorless oil, 1H NMR (CDCl3): 8.07 (d, J=8.8 Hz, 2H), 7.38-7.50 (m, 4H), 7.27 (m, 3H), 7.15 (m, 1H), 7.08 (d, J=8.8 Hz, 2H), 5.35 (s, 2H), 3.73 (dd, J=9.0, 7.5 Hz, 1H), 2.18 (m, 1H), 1.82 (m, 1H), 1.68 (s, 4H), 1.2-1.5 (m, 6H), 1.29 (s, 3H), 1.28 (s, 9H), 0.88 (t, J=7.5 Hz, 3H).

Workup

  1. additionwere added successively
  2. waitat room temperature for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe resulting filtrate was washed with 2 portions of 25 ml of water
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent evaporated
  7. customThe oil/solid residue was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dcc8934372d1461e8b7e7fc3ffa054c7
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

Loading…