Benzoate → Hexan-2-yl 4-hydroxybenzoate

HRID 2379656Notes

Reaction equation

HRID 2379656 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](N)[C:11]1C=[CH:15][CH:14]=[CH:13][CH:12]=1.ClCCl.C([OH:23])C>>[OH:23][C:5]1[CH:6]=[CH:7][C:2]([C:1]([O:9][CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH3:10])=[O:8])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 242BenzoateHCID 702EthanolHCID 6344DichloromethaneHCID 7504Benzylamine

Product 1

HCID 19365253Hexan-2-yl 4-hydroxybenzoateYield 100%

Procedure

Said benzoate (4.7 mmols) was dissolved in 20 ml of ethanol, and 9.7 mmols of benzylamine were added. The mixture was stirred overnight. To the reaction mixture was added 50 ml of dichloromethane. The organic layer was washed with a hydrochloric acid aqueous solution and water in this sequence. Subsequently, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel column chromatography to afford 1-methylpentyl p-hydroxybenzoate in a yield of 100%.

Workup

  1. washThe organic layer was washed with a hydrochloric acid aqueous solution and water in this sequence
  2. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce11df50853249ce974cb5e7a04889ad
Source dataset
uspto-grants-1994_11
Patent number
US05364560

Reaction notes

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