Vinyl Acetate → HCID 3803265, compound

HRID 2227110Notes

Reaction equation

HRID 2227110 reaction equation
[C:1]([O:4]C=C)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([CH:16]=[CH:17][CH:18]=[CH2:19])[CH2:12][CH2:13]CC>C1(C)C=CC=CC=1>[C:1]([O:4][CH:11]1[CH2:16][CH2:17][C:18]([CH3:19])=[CH:13][CH2:12]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 41971HCID 41971, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3803265HCID 3803265, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of vinyl acetate 4A (20 mL) in anhydrous toluene (220 mL) is added aluminum chloride (2.89 g). The flask is cooled to 0° C., and the isoprene 1C (R=methyl) (21.7 mL) is added dropwise. The reaction mixture is stirred 5 hours at 0° C., then allowed to stand at 4° C. for a further 16 hours. The reaction mixtire is then sequentially extracted with two portions (150 mL each) of 1% hydrochloric acid solution, water (75 mL), and brine (75 mL). It is dried over sodium sulfate, filtered through Celite, and concentrated in vacuo. The product is distilled to give 30 g of clear, colorless liquid.

Workup

  1. waitto stand at 4° C. for a further 16 hours
  2. extractionThe reaction mixtire is then sequentially extracted with two portions (150 mL each) of 1% hydrochloric acid solution, water (75 mL), and brine (75 mL)
  3. dry with materialIt is dried over sodium sulfate
  4. filtrationfiltered through Celite
  5. concentrationconcentrated in vacuo
  6. distillationThe product is distilled
  7. customto give 30 g of clear, colorless liquid

Sources & evidence

ORD record
ord-18f501d984b24e3083447518d18b89e1
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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