Acetic Acid → HCID 54152829, compound

HRID 358355Notes

Reaction equation

HRID 358355 reaction equation
C([Li])CCC.[CH3:6][O:7][P:8]([CH3:12])(=[O:11])[O:9][CH3:10].C[O:14][C:15](=O)[CH2:16][CH2:17][CH:18]=[C:19]([Cl:21])[CH3:20].C(O)(=O)C>O1CCCC1>[CH3:6][O:7][P:8]([CH2:12][C:15](=[O:14])[CH2:16][CH2:17][CH:18]=[C:19]([Cl:21])[CH3:20])(=[O:11])[O:9][CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 53775635HCID 53775635, compoundHCID 178418339Butyllithium

Product 1

HCID 54152829HCID 54152829, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

21.8 ml of n-butyllithium solution (2.2M in hexane) are added dropwise at -65° C. to a solution of 5.58 g of methanephosphonic acid dimethyl ester in 160 ml of absolute tetrahydrofuran and the mixture is stirred at that temperature for 15 minutes. A solution of 4.05 g of the methyl ester obtained in Example (6d) in 10 ml of tetrahydrofuran is then added and the mixture is stirred at -65° C. for 1 hour. The solution is heated to -10° C., 2.80 ml of acetic acid are added and the mixture is concentrated. The residue is partitioned between ethene and water, the ether phase is separated, dried over magnesium sulphate and concentrated in vacuo. The residue is then purified by ball-tube distillation. 4.23 g of the title compound are obtained (bath temperature 180°-185° C., 1.5 torr).

Workup

  1. stirringthe mixture is stirred at -65° C. for 1 hour
  2. concentrationthe mixture is concentrated
  3. customThe residue is partitioned between ethene and water
  4. customthe ether phase is separated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is then purified by ball-tube
  8. distillationdistillation

Sources & evidence

ORD record
ord-db5b13867121433099ef18c4b80cea19
Source dataset
uspto-grants-1984_08
Patent number
US04466969

Reaction notes

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