(Diethoxymethyl)benzene → HCID 59715043, compound

HRID 2223862Notes

Reaction equation

HRID 2223862 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH:10]([CH2:13][OH:14])[CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(O[CH:18](OCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:19]1([CH:18]2[O:12][CH2:11][CH:10]([C:4]3([CH2:3][CH2:2][OH:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[CH2:13][O:14]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 69884(Diethoxymethyl)benzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 59714891HCID 59714891, compound

Product 1

HCID 59715043HCID 59715043, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]propane-1,3-diol (200 mg) in N,N-dimethylformamide (8 mL) were added benzaldehyde diethyl acetal (752 mg) and p-toluenesulfonic acid pyridinium salt (48 mg) at room temperature. After stirring the solution at room temperature for 16 hours, saturated aqueous sodium bicarbonate solution was added thereto, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution (0.2 mL) and dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=4:6) to give the title compound (100 mg).

Workup

  1. extractionit was extracted with ethyl acetate
  2. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution (0.2 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=4:6)

Sources & evidence

ORD record
ord-2afb71769eaf4033bf793e357c208479
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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