3-Hydroxybenzaldehyde → HCID 11127426, compound

HRID 1827520Notes

Reaction equation

HRID 1827520 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 11127426HCID 11127426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-benzaldehyde (6.51 g, 53.3 mmol) and 3,4-dihydro-2H-pyran (7.3 mL, 80.0 mmol) in 150 mL methylene chloride was added pyridinium p-toluenesulfonate (1.34 g, 5.33 mmol). The reaction mixture was stirred at room temperature overnight. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate. The organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (5% ethyl acetate/hexanes to 10% ethyl acetate/hexanes) aforded 10.34 g (94%) of the title compound of Step A.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7722303f465841ffbea2f562739ca784
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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