Benzyl Chloride → 3-(Benzyloxy)-4-methoxybenzyl alcohol

HRID 1976554

Reaction equation

HRID 1976554 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6].CC([O-])(C)C.[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)CC>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 780893-Hydroxy-4-methoxybenzyl alcoholHCID 23665647Potassium tert-butoxide3×

Product 1

HCID 746223-(Benzyloxy)-4-methoxybenzyl alcoholYield 88.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 3-hydroxy-4-methoxy-benzyl alcohol (61.67 g, 400 mmole) in 1-propanol (600 ml) was treated at 60° C. with 97% t-BuOK (55.52 g, 480 mmole), at 90° C. with benzyl chloride (66.57 ml, 560 mmole) and the resulting mixture heated under reflux for 2 hours. Then at 90° C. a second batch of t-BuOK (9.25 g, 80 mmole) was added. After a further hour at reflux a third batch of t-BuOK (9.25 g, 80 mmol) and a second batch of benzyl chloride (9.51 ml, 80 mmole) was added at 90° C. After a further 2.5 hours at reflux the mixture was cooled to room temperature and the solid filtered off. The solvents were removed in vacuo, the residue treated with water (300 ml) and one-third of the solvent removed in vacuo. Water (100 ml) was added to the residue, which was then distilled off in vacuo and the procedure repeated. The resulting suspension was filtered, the solid was collected, dried and triturated with petroleum ether (2×600 ml) to give 3-benzyloxy-4-methoxy-benzyl alcohol, (86.21 g, 88.2%) mp 62-65° C.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter a further 2.5 hours at reflux the mixture
  4. filtrationthe solid filtered off
  5. customThe solvents were removed in vacuo
  6. additionthe residue treated with water (300 ml) and one-third of the solvent
  7. customremoved in vacuo
  8. additionWater (100 ml) was added to the residue, which
  9. distillationwas then distilled off in vacuo
  10. filtrationThe resulting suspension was filtered
  11. customthe solid was collected
  12. customdried
  13. customtriturated with petroleum ether (2×600 ml)

Sources & evidence

ORD record
ord-3dcb48659071488e86420061ef5104b4
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Linked notes

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