Benzyl Alcohol → HCID 54031137, compound

HRID 1110267Notes

Reaction equation

HRID 1110267 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7](C(O)=O)[CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.C([N:52]([CH2:55]C)CC)C.[CH2:57]([OH:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C1(C)C=CC=CC=1.CN(C=O)C>[C:58]1([CH2:57][O:64][C:55](=[O:40])[NH:52][C:7]2[CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19388988HCID 19388988, compound

Product 1

HCID 54031137HCID 54031137, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 g (6.7 mmol) of 3-acetyloxy-5-(octadecyloxy)benzenecarboxylic acid in 70 ml of dry toluene and 10 ml of dry DMF cooled in an ice bath was added 1.7 ml (8 mmol) of diphenylphosphoryl azide followed by 1.1 ml (8 mmol) of triethylamine. The reaction mixture was stirred in the ice bath for 1.5 hours and then was heated at 90° for 5 hours. Benzyl alcohol (20 ml) was added and heating at 90° was continued for 16 hours. The solvents were removed at reduced pressure and ethyl acetate was added to the residue. The extract was washed with NaHCO3 solution and then cooled at -18°. The precipitate was removed by filtration and the filtrate was concentrated at reduced pressure to an oil which was purified by chromatography on 150 g of silica gel using 25% ethyl acetate-hexane to give 1.87 g (50% yield, mp 57°-59 °) of 3-acetyloxy-5-(octadecyloxy)phenylcarbamic acid phenylmethyl ester.

Workup

  1. temperaturewas heated at 90° for 5 hours
  2. temperatureheating at 90°
  3. customThe solvents were removed at reduced pressure and ethyl acetate
  4. additionwas added to the residue
  5. washThe extract was washed with NaHCO3 solution
  6. temperaturecooled at -18°
  7. customThe precipitate was removed by filtration
  8. concentrationthe filtrate was concentrated at reduced pressure to an oil which
  9. customwas purified by chromatography on 150 g of silica gel using 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-cb092ecce14a4effa0eb2a49fba7f3a7
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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