Dimethylformamide → 1-(Chloromethyl)-4-Ethoxybenzene

HRID 2241853Notes

Reaction equation

HRID 2241853 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]O)=[CH:10][CH:9]=1)[CH3:6].CN(C=O)C>C(Cl)Cl>[CH2:5]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][Cl:3])=[CH:10][CH:9]=1)[CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 803454-Ethoxybenzyl alcohol

Product 1

HCID 20639711-(Chloromethyl)-4-Ethoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (10.4 g, 87.7 mmol) was added dropwise to a 0° C. solution of 4-ethoxybenzyl alcohol (11.0 g, 72.4 mmol) in dry CH2Cl2 (150 mL) with a catalytic amount of DMF (1 mL). Upon addition, reaction was allowed to stir for 5-10 minutes, while monitoring through TLC (CH2Cl2) for completion. Reaction mixture was concentrated under reduced pressure and the residue dissolved in minimal THF and then precipitated in cold H2O to yield a white precipitate. The solid was collected, taken up in CH2Cl2, dried and concentrated. The resulting oil was solidified by cooling with CO2/acetone. The compound as a white solid, which decomposes upon melting 11.3 g(92%).

Workup

  1. additionUpon addition, reaction
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionthe residue dissolved in minimal THF
  5. customprecipitated in cold H2O
  6. customto yield a white precipitate
  7. customThe solid was collected
  8. customdried
  9. concentrationconcentrated
  10. temperatureby cooling with CO2/acetone

Sources & evidence

ORD record
ord-d420a8d9b0794c439f253a9b260e8638
Source dataset
uspto-grants-2010_03
Patent number
US07671033B2

Reaction notes

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