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Benzyl Alcohol → 3,5-Bis(decyloxy)phenylcarbamic acid phenylmethyl ester

HRID 1110213
Notes
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Reaction equation

HRID 1110213 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:20]=1)C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.C([N:51]([CH2:54]C)CC)C.[CH2:56]([OH:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C1(C)C=CC=CC=1>[C:57]1([CH2:56][O:63][C:54](=[O:39])[NH:51][C:14]2[CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:20]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=2)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10320747Benzoic acid, 3,5-bis(decyloxy)-

Product 1

HCID 99847623,5-Bis(decyloxy)phenylcarbamic acid phenylmethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a stirred, ice bath cooled solution of 5.0 g (0.0115 mol) of 3,5-bis(decyloxy)benzoic acid in 100 ml of anhydrous toluene was added dropwise 3.0 ml (0.0138 mol) of diphenylphosphoryl azide followed by dropwise solution of 1.9 ml (0.0138 mol) of triethylamine. The reaction mixture was stirred in the ice bath for 75 minutes and then was heated at 90° for 2 hours. Benzyl alcohol (100 ml) was added and the solution was stirred and heated at 90° for 3.5 hours. The solvent was removed under reduced pressure and most of the excess benzyl alcohol was removed at 80°/0.1 mm. Sodium bicarbonate solution (100 ml) was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to an oil which was purified by HPLC using 25% hexane-ethyl acetate to give 4.87 g (79% yield) of 3,5-bis(decyloxy)phenylcarbamic acid phenylmethyl ester as an oil.

Workup

  1. temperaturewas heated at 90° for 2 hours
  2. temperatureheated at 90° for 3.5 hours
  3. customThe solvent was removed under reduced pressure and most of the excess benzyl alcohol
  4. customwas removed at 80°/0.1 mm
  5. additionSodium bicarbonate solution (100 ml) was added to the residue
  6. extractionthe product was extracted with ethyl acetate
  7. extractionThe dried extract
  8. concentrationwas concentrated at reduced pressure to an oil which
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-a8bf2df8cf444b3fbf6969c7b975e0fd
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05324747

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes