Lithium Hydroxide → 3-((Di-tert-butoxyphosphoryloxy)methyl)benzoic acid

HRID 1396035Notes

Reaction equation

HRID 1396035 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20]C)=[O:19])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.CO.O>[C:9]([O:8][P:6]([O:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([OH:20])=[O:19])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68385353Methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate

Product 1

HCID 683854873-((Di-tert-butoxyphosphoryloxy)methyl)benzoic acidYield 76.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate (0.1 g, 0.3 mmol) in THF (3 mL), methanol (3 mL), water (3 mL) was added lithium hydroxide (0.035 g, 0.81 mmol). The reaction mixture was stirred at rt for 1 h. After this time, the organic solvents were removed under reduced pressure, and EtOAc (30 mL) was added to the residual material followed by acetic acid (30%). The organic layer was washed with water (2×10 mL), dried over Na2SO4 and concentrated under vacuum to afford 3-((di-tert-butoxyphosphoryloxy)methyl)benzoic acid (80 mg, 0.23 mmol). 1H NMR (400 MHz, DMSO-d6): 1.41 (s, 18H), 5.00 (d, J=8, 2H), 7.52 (t, J=7.6, 1H), 7.62 (d, J=7.6, 1H), 7.90 (d, J=8.0, 1H), 7.99 (s, 1H). LCMS-m/z: 343.2.

Workup

  1. customAfter this time, the organic solvents were removed under reduced pressure, and EtOAc (30 mL)
  2. additionwas added to the residual material
  3. washThe organic layer was washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3d3437a8e64142e1ae0feed5f637d518
Source dataset
uspto-grants-2014_12
Patent number
US08901106B2

Reaction notes

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