1-Dodecene → 3-Benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid

HRID 2050701Notes

Reaction equation

HRID 2050701 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:13]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][P:27]([OH:29])[OH:28])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:13]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][P:27]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:28])[OH:29])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 81831-DodeceneHCID 190908943-Benzyloxycarbonylaminopropylphosphonous acid

Product 1

HCID 190908573-Benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.30 g of dodecene in 6 ml of dry toluene is heated to 80° under an atmosphere of argon. To this solution a suspension of 2.0 g of 3-benzyloxycarbonylaminopropylphosphonous acid in 30 ml of dry toluene containing 0.6 g of t-butylcyclohexylperdicarbonate is added within 15 minutes. The reaction mixture is then stirred at 80° for 2 hours. An additional amount of 0.6 g of the radical initiator is added and stirring at 80° is continued for 2 hours. Then, the reaction mixture is cooled to room temperature and the solvent is removed by means of a rotary evaporator. The residue is triturated with petroleum ether (60-80°), filtered and dried to give 3-benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid as a white solid, m.p. 115-6°; 31P-NMR: δ=+58.7 ppm (CDCl3).

Workup

  1. additionof t-butylcyclohexylperdicarbonate is added within 15 minutes
  2. stirringstirring at 80°
  3. waitis continued for 2 hours
  4. customthe solvent is removed by means of a rotary evaporator
  5. customThe residue is triturated with petroleum ether (60-80°)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-5e98720bfdb04bcaa2fddc332ea63797
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

Loading…