Dimethylformamide → Benzoic acid 3,5-dimethyl-benzyl ester

HRID 426171

Reaction equation

HRID 426171 reaction equation
ClC1N=C(Cl)C(C(C)C)=C(O[C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)N=1.[C:21]([O-:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+].[CH3:31]N(C=O)C>>[CH3:20][C:15]1[CH:16]=[C:17]([CH:18]=[C:13]([CH3:31])[CH:14]=1)[CH2:19][O:28][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 517055Sodium BenzoateHCID 189252522,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine

Product 1

HCID 13146856Benzoic acid 3,5-dimethyl-benzyl esterYield 71%

Procedure

A mixture of 3,5-dimethylbenzyl bromide (2, 39.8, 0.2M) and sodium benzoate (34.56 g, 0.24M) in anhydrous DMF (400 ml) was stirred at room temperature for overnight. The mixture was then partitioned between ether and water. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow oil. The crude product was purified by silica gel column chromatography (eluent, hexane) to afford 32 g (71%) of a colorless oil. 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.29 (2H, s), 6.98 (1H, s), 7.05 (2H, s), 7.38-7.59 (3H, m), 8.05-8.11 (2H, m).

Workup

  1. customThe mixture was then partitioned between ether and water
  2. washwashed with water twice
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a pale yellow oil
  7. customThe crude product was purified by silica gel column chromatography (eluent, hexane)

Sources & evidence

ORD record
ord-5017029fa6f4407a94fe37d947e3f597
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Linked notes

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