Benzene → Neophyl acetate

HRID 413540Notes

Reaction equation

HRID 413540 reaction equation
[C:1]([O:4][CH2:5][C:6](=[CH2:8])[CH3:7])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:1]([O:4][CH2:5][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:7])[CH3:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 241Benzene2×HCID 699622-Methylallyl acetateHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 303084Neophyl acetate

Conditions

Temperature
5 °C

Procedure

Mix methallyl acetate (228 g, 2.0 mol) and benzene (1L) and cool to 5° C. Add aluminum chloride (266 g, 2.0 mol) over approximately 30 minutes while maintaining the temperature below 10° C. Add, in portions of 50 mL to 80 mL each, to a 5° C. mixture of aluminum chloride (15 g) in benzene (600 mL). After addition is complete, stir at 0-3° C. for ½ hour, pour onto ice (2 kg) and separate the organic layer. Wash with water (2×300 mL), dry (Na2SO4), and distill to give neophyl acetate.

Workup

  1. additionAdd, in portions of 50 mL to 80 mL each, to a 5° C.
  2. additionAfter addition
  3. additionpour onto ice (2 kg)
  4. customseparate the organic layer
  5. washWash with water (2×300 mL)
  6. dry with materialdry (Na2SO4)
  7. distillationdistill

Sources & evidence

ORD record
ord-b7afb9c306fb4881bb786340eb4db4f9
Source dataset
uspto-grants-2003_05
Patent number
US06566526B2

Reaction notes

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