Tributyl phosphite → Dibutyl 4-benzyloxybenzylphosphonate

HRID 1488341Notes

Reaction equation

HRID 1488341 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:21][P:22]([O:28]CCCC)[O:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:19][CH3:20]>>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][P:22](=[O:28])([O:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:21][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7623Tributyl phosphiteHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 22904634Dibutyl 4-benzyloxybenzylphosphonate

Conditions

Temperature
50 °C

Procedure

A mixture of 4-benzyloxybenzyl chloride (4.99 g) and tri-n-butylphosphite is heated at 50° C. for about 4 hours while removing butyl chloride. The mixture is cooled to room temperature and the crude product purified by HPLC on silica, eluting with 25% ethyl acetate in hexane, to give dibutyl 4-benzyloxybenzylphosphonate.

Workup

  1. customwhile removing butyl chloride
  2. temperatureThe mixture is cooled to room temperature
  3. customthe crude product purified by HPLC on silica
  4. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b7147a46d7644a8d9099f48843f6d485
Source dataset
uspto-grants-1997_10
Patent number
US05674482

Reaction notes

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