Phosphoric Acid → HCID 67544534, compound

HRID 885463Notes

Reaction equation

HRID 885463 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[CH2:11][OH:12].P(=O)(O)(O)O>C(OC(=O)C)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:2]2[C:3]3[C:4](=[CH:5][C:6]([C:7]#[N:8])=[CH:9][CH:10]=3)[CH2:11][O:12]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 67545291HCID 67545291, compound

Product 1

HCID 67544534HCID 67544534, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

33.82 g (125.6 mmol) of the 4-{hydroxy(4-methoxyphenyl)methyl}-3-(hydroxymethyl)benzonitrile prepared in step 2 was dissolved in 150 ml of ethylacetate, and 150 ml of a 85% aqueous solution of phosphoric acid was added at room temperature. The mixture was raised to 80° C. and stirred for 3 hrs. The reaction mixture was then cooled again to room temperature, and washed with water and saturated NaCl solution. An organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was treated with 2-propanol to afford 18.0 g of a white solid (yield: 57%).

Workup

  1. temperatureThe reaction mixture was then cooled again to room temperature
  2. washwashed with water and saturated NaCl solution
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. additionThe residue was treated with 2-propanol

Sources & evidence

ORD record
ord-14f696a0c9f14625ad1989e47d5e60d0
Source dataset
uspto-grants-2012_08
Patent number
US08242159B2

Reaction notes

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