4-Methylbenzaldehyde → Di(tert-butyl) hydroxy(4-methylphenyl)methylphosphonate

HRID 566490

Reaction equation

HRID 566490 reaction equation
[C:1]([O:5][P:6]([O-:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Li]N([Si](C)(C)C)[Si](C)(C)C.[C:23]1([CH3:31])[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=1>C1COCC1>[OH:30][CH:29]([P:6](=[O:12])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[C:26]1[CH:27]=[CH:28][C:23]([CH3:31])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 21959072Di-tert-butyl phosphiteHCID 178418261HCID 178418261, compound

Product 1

HCID 86756235Di(tert-butyl) hydroxy(4-methylphenyl)methylphosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of di-tert-butylphosphite (30 g) in THF (700 mL) cooled at −78° C. was added dropwise a solution of LiN(TMS)2 (165 mL, 1M in THF). After stirring for 30 min at −78° C., a solution of 4-tolualdehyde (18 mL in 100 mL of THF) was added. The reaction mixture was stirred for 30 min at −78° C. and 2 h at 0° C., and then quenched with 400 mL of 50% saturated aqueous NH4Cl solution. The mixture was extracted with 1 L of 2:1 hexane/EtOAc and the extract was dried over Na2SO4. After concentration and swishing from hexane, 32 g of the title compound was obtained as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 30 min at −78° C. and 2 h at 0° C.
  2. customquenched with 400 mL of 50% saturated aqueous NH4Cl solution
  3. extractionThe mixture was extracted with 1 L of 2:1 hexane/EtOAc
  4. dry with materialthe extract was dried over Na2SO4
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-67fd5c6a7428426fb8d9a079d85952f9
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Linked notes

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