Methanol → (2-Ethylphenyl)acetaldehyde

HRID 2287479Notes

Reaction equation

HRID 2287479 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH3:11])[CH:2]=C.C[OH:13]>C(Cl)Cl>[CH2:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]=[O:13])[CH3:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 186945043-(2-Ethylphenyl)-1-propene

Product 1

HCID 45117183(2-Ethylphenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 54.05 g of the crude 1-allyl-2-ethylbenzene in 500 mL of 1:1 CH2Cl2 --CH3OH was cooled to -78° C. A stream of O3 was bubbled through the solution for 3 h, until all of the starting material had disappeared. Then a stream of air was bubbled through the solution until the blue color had faded. A total of 25 mL of methyl sulfide was added and the solution was stirred at room temperature for 1 h. The solution was concentrated and dried under vacuum to afford (2-ethylphenyl) acetaldehyde as a colorless oil which was used directly in the next step.

Workup

  1. customA stream of O3 was bubbled through the solution for 3 h
  2. customThen a stream of air was bubbled through the solution until the blue color
  3. additionA total of 25 mL of methyl sulfide was added
  4. concentrationThe solution was concentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b3450c4e848e46249f8835f1e8a263db
Source dataset
uspto-grants-2000_07
Patent number
US06083980

Reaction notes

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