Lithium hydroxide, monohydrate → 2-(3-(Diethoxyphosphoryl)phenyl)acetic acid

HRID 1525327Notes

Reaction equation

HRID 1525327 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:10]=[C:11]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:12]=[CH:13][CH:14]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].O[Li].O>C(O)C.O>[CH2:7]([O:6][P:4]([C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89462900Ethyl 2-(3-(diethoxyphosphoryl)phenyl)acetate2×

Product 1

HCID 894625312-(3-(Diethoxyphosphoryl)phenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(3-(diethoxyphosphoryl)phenyl)acetate, 35i-c, (26 g, 86.7 mmol) and LiOH.H2O (5.5 g, 130 mmol) in ethanol (40 mL) and H2O (40 mL) was stirred overnight. The resulting mixture was concentrated and washed by ethyl acetate. The aqueous layers were adjusted to about pH 1-2 with HCl. The mixture was extracted by ethyl acetate. The combined organic layers were washed by brine, dried over Na2SO4 and concentrated to afford the title compound, 35i-d, as brown oil (19 g, 81%). 1H NMR (300 MHz, CDCl3) δ1.15-1.25 (m, 6H), 3.68 (s, 2H), 3.95-4.06 (m, 4H), 7.43-7.64 (m, 4H), 12.32 (s, 1H). LC-MS (M+H)+ 273.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. washwashed by ethyl acetate
  3. extractionThe mixture was extracted by ethyl acetate
  4. washThe combined organic layers were washed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2952de4acf1141b78c6a7e38168127bd
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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