4-Methoxybenzyl alcohol → 4-Methoxybenzaldehyde

HRID 399612

Reaction equation

HRID 399612 reaction equation
[CH2:1]([OH:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].ClN1C(=O)C(C)(C)N(Cl)C1=O.ClC1C=CC(OC)=CC=1>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([CH:1]=[O:10])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 121674-ChloroanisoleHCID 517045Sodium Acetate

Product 1

HCID 312444-MethoxybenzaldehydeYield 91.1%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5 g (36.2 mmol) of anisyl alcohol, 3.0 g (36.6 mmol) of sodium acetate and 4.2 g (21.3 mmol) of dichlorodimethylhydantoin were suspended in 40 ml of methylene chloride in a 100 ml sulphonation flask. The suspension was cooled to 0° C. while stirring and treated with 10 mg (0.06 mmol) of TEMPO, whereupon the mixture was held at 0° C. for 16 hours. Thereafter, the reaction had finished without 4-chloro-anisole being formed in any amount worth mentioning. The white precipitate was filtered off and the filtrate was washed with sodium bicarbonate solution and with sodium chloride solution. Distillation of the crude product gave 4.49 g (91%) of anisaldehyde GC content: 88.8% (area percent).

Workup

  1. customformed in any amount
  2. filtrationThe white precipitate was filtered off
  3. washthe filtrate was washed with sodium bicarbonate solution and with sodium chloride solution
  4. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-7fb77186813d48168788ca19dfc8ce42
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Linked notes

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