Benzyl Chloride → HCID 22372525, compound

HRID 439687Notes

Reaction equation

HRID 439687 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([Cl:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[Cl-:32].[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[C:8]([O:10][CH2:11][CH2:12][CH2:13][N+:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:15])[CH3:16])=[O:9])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 22407754HCID 22407754, compound

Product 1

HCID 22372525HCID 22372525, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 33.55 g (100 mmol) of 3-dimethylaminopropyl 3,5-di-tert-butyl-4-hydroxybenzoate prepared as described above and 12.66 g (100 mmol) of benzyl chloride in 140 ml of acetonitrile was heated at reflux for 1 hour and 15 minutes and then concentrated under vacuum to a clear, thick oil. The resultant oil was allowed to stand overnight and crystallized. The solid was washed with ether, collected and dried giving 45.2 g (97.8% of theory) of N-[3-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)propyl]-N,N-dimethylbenzylammonium chloride.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour and 15 minutes
  3. concentrationconcentrated under vacuum to a clear, thick oil
  4. customcrystallized
  5. washThe solid was washed with ether
  6. customcollected
  7. customdried

Sources & evidence

ORD record
ord-6c77ccbc7adb4d108ad5cbd0293e352f
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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