Isobutyraldehyde → HCID 20037262, compound

HRID 1904537Notes

Reaction equation

HRID 1904537 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16](=O)[CH:17]([CH3:19])[CH3:18]>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[CH2:16][C:17]([CH3:19])([CH3:18])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6561IsobutyraldehydeHCID 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 20037262HCID 20037262, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

3-Benzyloxyphenol (5.0 g), 2.0 g of isobutyraldehyde, 0.1 g of methanesulfonic acid and 50 ml of toluene were put into a flask equipped with the Dean-Stark condenser, and stirred under reflux for 4 hours. Low-boiling compounds were evaporated under reduced pressure. The residue was purified by column chromatography to give 3.8 g of 6-benzyloxy-2,3-dihydro-2,2-dimethylbenzofuran as a brown liquid. This product was dissolved in ethanol, and 0.4 g of 5% palladium-carbon was added. The mixture was stirred at room temperature for 8 hours in an atmosphere of hydrogen. The catalyst was separated by filtration, and the filtrate was concentrated. The residue was purified by column chromatography to give 2.0 g (yield 50%) of the desired product as a pale yellow liquid.

Workup

  1. customequipped with the Dean-Stark condenser
  2. temperatureunder reflux for 4 hours
  3. customLow-boiling compounds were evaporated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4cebf6df1e1146ab82b00ac5409d3045
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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