Water → 5-(1-Hydroxy-1-methylethyl)-2-methoxybenzaldehyde

HRID 1599442Notes

Reaction equation

HRID 1599442 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=[O:6])C=1C#N)#N.[CH:15]([C:18]1[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=1)[CH:23]=[O:24])([CH3:17])[CH3:16].O.CCOCC>C(Cl)Cl>[OH:6][C:15]([C:18]1[CH:19]=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=1)[CH:23]=[O:24])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 70095025-ISOPROPYL-2-METHOXYBENZALDEHYDE

Product 1

HCID 189286345-(1-Hydroxy-1-methylethyl)-2-methoxybenzaldehydeYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DDQ (10.07 g, 44.36 mmol) was added to a solution of 5-isopropyl-2-methoxybenzaldehyde (2.63 g, 15.3 mmol) dissolved in methylene chloride (100 ml) contained water (10 ml) at room temperature, and the resulting mixture was stirred for 24 h. Ether (200 ml) was added to the reaction mixture, and insoluble materials were removed by filtration. The filtrate was washed with aq. sodium thiosulfate solution, aq. sodium carbonate solution, and brine, successively and dried over magnesium sulfate. After evaporation of the solvent the resultant yellow oil was purified by chromatography (silica gel, 2-70% ethyl acetate/hexane) to afford pure 5-(1-hydroxy-1-methylethyl)-2-methoxybenzaldehyde (498 mg, 17%) as a slightly yellow oil and 5-(1-methoxy-1-methylethyl)-2-methoxybenzaldehyde (less polar, 129 mg, 4%) as a solid.

Workup

  1. customat room temperature
  2. customwere removed by filtration
  3. washThe filtrate was washed with aq. sodium thiosulfate solution, aq. sodium carbonate solution, and brine
  4. dry with materialsuccessively and dried over magnesium sulfate
  5. customAfter evaporation of the solvent the resultant yellow oil
  6. customwas purified by chromatography (silica gel, 2-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3405e9047977485f969e72ae51dfcafb
Source dataset
uspto-grants-1998_04
Patent number
US05741797

Reaction notes

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