Hydrochloric Acid → 4-Methyloxybenzyl chloride

HRID 1290101Notes

Reaction equation

HRID 1290101 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.[ClH:11]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 77384-Methoxybenzyl alcohol

Product 1

HCID 699934-Methyloxybenzyl chloride

Procedure

4-Methoxybenzylalcohol (50 g, 0.36 mol) (Aldrich) was added dropwise to 100 mL of conc. HCl and stirred vigorously for 2 h at rt. The reaction mixture was extracted four times with Et2O, the Et2O extracts were combined, washed with brine, dried (Na2SO4), and concentrated. The yellow oil was distilled at 70°-73° C. (0.2 mmHg) to give 52 g (93%) as a colorless oil: 1H NMR (CDCl3) d 3.85 (s, 3H, OCH3), 4.62 (s, 2H, CH2Cl), 6.91-6.93 (d, 2H, J=8 Hz, ArH), 7.38-7.40 (d, 2H, J=8 Hz, ArH) ; MS(FD) 156(M+).

Workup

  1. extractionThe reaction mixture was extracted four times with Et2O
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. distillationThe yellow oil was distilled at 70°-73° C. (0.2 mmHg)
  6. customto give 52 g (93%) as a colorless oil

Sources & evidence

ORD record
ord-a82818e8cb1846119ecf5e3eac0e44a8
Source dataset
uspto-grants-1998_05
Patent number
US05750708

Reaction notes

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