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

HRID 1633106Notes

Reaction equation

HRID 1633106 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-b09d806e927d49cfac6f729feaf822fc
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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