Trimethyl phosphite → Dimethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate

HRID 48923Notes

Reaction equation

HRID 48923 reaction equation
[I-].C[N+](C)(C)[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[P:17]([O:22]C)([O:20][CH3:21])[O:18][CH3:19]>C1(C)C(C)=CC=CC=1>[OH:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([CH2:4][P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19])=[CH:6][C:7]=1[O:13][CH3:14]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 20634507Trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodide

Product 1

HCID 86585635Dimethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonateYield 83%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodide (1 g, 3.0 mmol) was suspended in 8 ml xylene, trimethyl phosphite (0.52 ml, 4.4 mmol) was added dropwise and the resulting mixture was refluxed for 14 h. The solid formed was filtered and the solvent and excess of phosphite were evaporated under vacuum to yield dimethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate as a viscous oil (0.64 g, 83%).

Workup

  1. temperaturethe resulting mixture was refluxed for 14 h
  2. customThe solid formed
  3. filtrationwas filtered
  4. customthe solvent and excess of phosphite were evaporated under vacuum

Sources & evidence

ORD record
ord-391ab93039044ba0a2ab64e6470e1512
Source dataset
uspto-grants-2004_03
Patent number
US06706698B2

Reaction notes

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