Dimethylformamide → 1-(Chloromethyl)-4-(dodecyloxy)benzene

HRID 2241857Notes

Reaction equation

HRID 2241857 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]O)=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CN(C=O)C>C(Cl)Cl>[CH2:5]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][Cl:3])=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 144776284-Dodecyloxybenzyl alcohol

Product 1

HCID 100867551-(Chloromethyl)-4-(dodecyloxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (38.8 g, 328 mmol) was added dropwise to a 0° C. solution of 4-Dodecyloxybenzyl alcohol (80.0 g, 274 mmol) in dry CH2Cl2 (900 mL) with a catalytic amount of DMF. 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 resulting residue re-crystallized from acetone to give the title benzyl chloride, decomposes upon melting. 77g (92%).

Workup

  1. additionUpon addition, reaction
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe resulting residue re-crystallized from acetone

Sources & evidence

ORD record
ord-65249160dbb342c5ac3823c7b831d404
Source dataset
uspto-grants-2010_03
Patent number
US07671033B2

Reaction notes

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