Benzyl Alcohol → 3-(Octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester

HRID 1110248Notes

Reaction equation

HRID 1110248 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]=1)C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])C=CC=CC=1.C([N:59]([CH2:62]C)CC)C.[CH2:64]([OH:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>C1(C)C=CC=CC=1>[C:65]1([CH2:64][O:71][C:62](=[O:47])[NH:59][C:22]2[CH:26]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:28]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=2)[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 152328343-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid

Product 1

HCID 152328353-(Octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 10.7 g (0.02 mol) 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid in 250 ml of anhydrous toluene cooled in an ice bath was added 5.1 ml (0.024 mol) of diphenylphosphoryl azide followed by 3.8 ml (0.028 mol) of triethylamine. The reaction mixture was stirred in an ice bath for 1 hour and then heated at 90° for 2 hours. After cooling to room temperature, 70 ml of benzyl alcohol was added. The reaction mixture was then stirred and heated at 90° for 18 hours. The solvent was removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with saturated NaHCO3 solution, dried and concentrated to an oil which was purified by HPLC using 10% ethyl acetate-hexane to give 10.9 g (85% yield, mp 68°-69°) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureheated at 90° for 2 hours
  3. stirringThe reaction mixture was then stirred
  4. temperatureheated at 90° for 18 hours
  5. customThe solvent was removed at reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe extract was washed with saturated NaHCO3 solution
  8. customdried
  9. concentrationconcentrated to an oil which
  10. customwas purified by HPLC

Sources & evidence

ORD record
ord-af9fdb79a9d94924a06aa293a2b1eaaa
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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