Triethylamine → 1-(Chloromethyl)-4-methoxy-2-methylbenzene

HRID 2368913Notes

Reaction equation

HRID 2368913 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[C:5]([CH3:11])[CH:4]=1.C(N(CC)CC)C.CS([Cl:23])(=O)=O>C1(C)C=CC=CC=1>[Cl:23][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27595864-Methoxy-2-methylbenzyl alcohol

Product 1

HCID 110520871-(Chloromethyl)-4-methoxy-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (4-methoxy-2-methylphenyl)methanol (8.2 g, 54.0 mmol) and triethylamine (9.1 mL, 65.0 mmol) in toluene (100 mL) at 0° C., methanesulfonyl chloride (5.1 mL, 65.0 mmol) was added via syringe over 20 min. The ice water bath was removed, and the reaction was allowed to stir at room temperature for 30 min, heated at 80° C. for 3 days, and then concentrated. The reaction was diluted with DCM, washed with H2O (3×100 mL) and brine, dried over Na2SO4, and concentrated under reduced pressure to 1-(chloromethyl)-4-methoxy-2-methylbenzene (8.1 g) as a dark brown oil. 1H NMR (300 MHz, CDCl3): δ 7.25 (d, 1H), 6.75 (m, 2H), 4.62 (s, 2H), 3.82 (s, 3H), 2.43 (s, 3H).

Workup

  1. customThe ice water bath was removed
  2. temperatureheated at 80° C. for 3 days
  3. concentrationconcentrated
  4. additionThe reaction was diluted with DCM
  5. washwashed with H2O (3×100 mL) and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure to 1-(chloromethyl)-4-methoxy-2-methylbenzene (8.1 g) as a dark brown oil

Sources & evidence

ORD record
ord-5d6f2a35673a4b468cac7794bd9a9344
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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