4-Methoxybenzyl alcohol → 4-Methoxybenzaldehyde

HRID 1272591Notes

Reaction equation

HRID 1272591 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].C1C(=O)N(Cl)C(=O)C1>[Br-].C([N+](C)(C)C)C1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1.ClCCl>[CH:9](=[O:10])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 10340Sodium CarbonateHCID 31398Chlorosuccinimide

Product 1

HCID 312444-MethoxybenzaldehydeYield 82.1%

Reagents, catalysts & solvents 3

HCID 21449Benzyltrimethylammonium bromideCatalystHCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Methoxybenzyl alcohol (2.0 g, 14.5 mmol), sodium carbonate (0.9 g, 8.7 mmol), TEMPO (23 mg, 0.15 mmol), benzyltrimethylammonium bromide (0.3 g, 1.5 mmol) and dichloromethane (15 ml) were put in a 50-ml egg plant type flask. The suspension was cooled to less than 10° C. in an ice bath and thereto was added NCS (2.1 g, 16 mmol) divided in two portions. The insoluble materials were filtered off and the filtrate was washed with 5% aqueous sodium bicarbonate solution. The crude product was purified by distillation to give p-anisaldehyde (1.62 g, yield 82%).

Workup

  1. temperatureThe suspension was cooled to less than 10° C. in an ice bath
  2. filtrationThe insoluble materials were filtered off
  3. washthe filtrate was washed with 5% aqueous sodium bicarbonate solution
  4. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-fde65103bc6d4a2587e9f50b7335da7f
Source dataset
uspto-grants-2007_04
Patent number
US07208634B2

Reaction notes

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