Sodium hydride → 1-(4-Pivaloyloxymethyloxycarbonylphenyl)propan-2-one

HRID 1906960Notes

Reaction equation

HRID 1906960 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)[C:4]([CH3:6])=[O:5].[C:16]([O:22][CH2:23]Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[C:16]([O:22][CH2:23][O:12][C:11]([C:10]1[CH:14]=[CH:15][C:7]([CH2:3][C:4](=[O:5])[CH3:6])=[CH:8][CH:9]=1)=[O:13])(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 5762444-(2-Oxopropyl)benzoic acid

Product 1

HCID 201341841-(4-Pivaloyloxymethyloxycarbonylphenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium hydride (0.48 g) was added to 4-acetonylbenzoic acid (3.56 g) in acetonitrile and the solution refluxed for 1/2 hour. Chloromethyl pivalate (3.02 g) was then added and the mixture refluxed for 22 hours. Acetonitrile was removed, the residue partitioned between ether and water and the organic layer separated and washed with sodium bicarbonate solution (×2). The ether layer was dried (MgSO4) and evaporated to give the title compound which was crystallised and recrystallised from hexane. τ(CDCl3) 8.77 (9H, s), 7.82 (3H, s), 6.25 (2H, s), 4.02 (2H, s), 2.73 (2H, d, J=9 Hz), 1.96 (2H, d, J=9 Hz).

Workup

  1. temperaturethe solution refluxed for 1/2 hour
  2. temperaturethe mixture refluxed for 22 hours
  3. customAcetonitrile was removed
  4. customthe residue partitioned between ether and water
  5. customthe organic layer separated
  6. washwashed with sodium bicarbonate solution (×2)
  7. dry with materialThe ether layer was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-776541c2a1bb45c4b1ec6d35e91b2fdd
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

Loading…