Methylparaben → HCID 59906461, compound

HRID 2374223Notes

Reaction equation

HRID 2374223 reaction equation
O[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O:14][P:15](COS(C(F)(F)F)(=O)=O)([O:17]CC)=[O:16])C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[P:15]([C:10]1[CH:11]=[CH:2][CH:3]=[CH:4][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([OH:17])([OH:16])=[O:14]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonate

Product 1

HCID 59906461HCID 59906461, compoundYield 139.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-hydroxybenzoate 111 (0.977 g, 6.42 mmol) and trifluoro-methanesulfonic acid diethoxy-phosphorylmethl ester (2.12 g, 7.06 mmol) in THF (50 mL) was treated with Cs2CO3 (4.18 g, 12.84 mmol). The resulting reaction mixture was stirred for 1 h at room temperature before it was partitioned between EtOAc and sat. aqueous NH4Cl and extracted with EtOAc (3×). The organic phase was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. Purification of the crude product on silica gel (eluted with 60-90% EtOAc/hexane) provided 1.94 g (quantitative) of methyl phosphonobenzoate compound 112 as a clear oil.

Workup

  1. customThe resulting reaction mixture
  2. customwas partitioned between EtOAc and sat. aqueous NH4Cl
  3. extractionextracted with EtOAc (3×)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customPurification of the crude product on silica gel (eluted with 60-90% EtOAc/hexane)

Sources & evidence

ORD record
ord-883892b0263f463eb2b72ac6c6893c66
Source dataset
uspto-grants-2008_12
Patent number
US07462608B2

Reaction notes

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