3,4-dihydro-2H-pyran → HCID 10823699, compound

HRID 1798306Notes

Reaction equation

HRID 1798306 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 251690o-OrsellinaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 10823699HCID 10823699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 250-mL round-bottom flask were placed a solution of 2,4-dihydroxy-6-methylbenzaldehyde (2.0 g, 13.16 mmol, 1.00 equiv) in dichloromethane (50 mL), 3,4-dihydro-2H-pyran (1.65 g, 19.64 mmol, 1.49 equiv) and pyridinium p-toluenesulfonate (330 mg, 1.31 mmol, 0.10 equiv). The resulting solution was stirred overnight at room temperature. Then it was diluted with 100 mL of dichloromethane and washed with 3×20 mL of 1 M sodium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.8 g (52%) of 2-hydroxy-6-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde as a yellow oil.

Workup

  1. customInto a 250-mL round-bottom flask were placed
  2. washwashed with 3×20 mL of 1 M sodium carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThis resulted in 1.8 g (52%) of 2-hydroxy-6-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde as a yellow oil

Sources & evidence

ORD record
ord-9c2d2344d5df47fc9cadb1f77d6e1647
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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