Hydrochloric Acid → HCID 23021517, compound

HRID 501789Notes

Reaction equation

HRID 501789 reaction equation
[CH:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([OH:14])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.IC.[C:17](=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([O:14][CH3:17])[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23021572HCID 23021572, compound

Product 1

HCID 23021517HCID 23021517, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

0.770 g of 4-cyclopentyl-2-hydroxybenzaldehyde, 0.38 mL of iodomethane, and 0.839 g of potassium carbonate were suspended in 7.7 mL of N,N-dimethylformamide, and this mixture was stirred for 2 hours at 75° C. The reaction mixture, which was cooled to room temperature, was added to a mixture of ethyl acetate and water, and then adjusted to pH 3 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 0.777 g of 4-cyclopentyl-2-methoxybenzaldehyde as yellow oil.

Workup

  1. temperatureThe reaction mixture, which was cooled to room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-1b67023f3afd42ea9638daaf08487f89
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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