Benzyl Chloride → HCID 15277884, compound

HRID 439683Notes

Reaction equation

HRID 439683 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([Cl:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[Cl-:31].[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([O:10][CH2:11][CH2:12][N+:13]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:15])[CH3:14])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 15277883HCID 15277883, compound

Product 1

HCID 15277884HCID 15277884, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 32.15 g (100 mmol) of 2-dimethylaminoethyl 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 then concentrated after filtering off a small amount of insolubles. The viscous residue was treated with boiling heptane and then with ligroine. The resultant amorphous solid was allowed to stand in ether which induced crystallization. This solid was collected and dried giving 38.2 g of N-[2-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)ethyl]-N,N-dimethylbenzylammonium chloride (85.26% of theory); mp=215° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated
  4. filtrationafter filtering off a small amount of insolubles
  5. additionThe viscous residue was treated with boiling heptane
  6. customcrystallization
  7. customThis solid was collected
  8. customdried

Sources & evidence

ORD record
ord-2d7e796681c34bd593539fefbcae2c21
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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