tert-Butanol → 2-Chloro-3,5-dimethoxybenzaldehyde

HRID 1096830Notes

Reaction equation

HRID 1096830 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C)(C)C.[Cl:28][C:29]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([O:39][CH3:40])=[CH:33][C:30]=1[CH2:31][OH:32].CCOC(C)=O>C(Cl)Cl>[Cl:28][C:29]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([O:39][CH3:40])=[CH:33][C:30]=1[CH:31]=[O:32]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 66783901HCID 66783901, compound

Product 1

HCID 179956172-Chloro-3,5-dimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of Dess-Martin periodinane (1.38 g, 32.5 mmol) in CH2Cl2 (120 mL) was added tert-butanol (3.05 mL, 32.5 mmol). After stirring for 15 min, a sol. of 2-chloro-3,5-dimethoxybenzyl alcohol (H. Newman, R. B. Angier, J. Org. Chem., 1966, 31, 1462-1464, 5.06 g, 25.0 mmol) in CH2Cl2 (20 mL) was added. After stirring for 1 h, EtOAc (200 mL) was added and the mixture was washed with aq. 1M NaOH. The org. phase was evaporated, and the crude product was dissolved again in EtOAc (200 mL), and washed successively with aq. 1M NaOH (2×), water (2×) and brine. The org. phase was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The aldehyde was used without further purification. LC-MS: tR=0.92 min.

Workup

  1. stirringAfter stirring for 1 h
  2. washthe mixture was washed with aq. 1M NaOH
  3. customphase was evaporated
  4. dissolutionthe crude product was dissolved again in EtOAc (200 mL)
  5. washwashed successively with aq. 1M NaOH (2×), water (2×) and brine
  6. dry with materialphase was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customThe aldehyde was used without further purification

Sources & evidence

ORD record
ord-4374fbbcc35842548c8d7420bed2bbef
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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