HCID 66978185, compound → HCID 11521317, compound

HRID 2108929Notes

Reaction equation

HRID 2108929 reaction equation
C([O:8][C:9]1[C:10]([CH3:22])=[C:11]([CH3:21])[C:12]2[O:17][C:16]([CH3:19])([CH3:18])[O:15][CH2:14][C:13]=2[CH:20]=1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[CH3:18][C:16]1([CH3:19])[O:15][CH2:14][C:13]2[CH:20]=[C:9]([OH:8])[C:10]([CH3:22])=[C:11]([CH3:21])[C:12]=2[O:17]1

Participants

5

Reactant 2

HCID 66978185HCID 66978185, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11521317HCID 11521317, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-benzyloxy-2,2,7,8-tetramethyl-4H-benzo[1,3]dioxine (86 mg, 0.29 mmol) in 10 mL EtOH was added Pd/C (15 mg, 10%). It was stirred in a hydrogen atmosphere for 1.5 h and filtered. The solution was concentrated and the crude product was purified on silicagel column chromatography to afford 2,2,7,8-tetramethyl-4H-benzo[1,3]dioxin-6-ol as a white solid (54 mg). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 6.28 (s, 1H), 4.77 (s, 1H), 4.76 (s, 2H), 2.17 (s, 3H), 2.13 (s, 1H), 1.55 (s, 3H), 1.54 (s, 3H); 13C-NMR δ (ppm): 147.1, 142.9, 126.1, 122.7, 116.6, 107.5, 99.1, 60.9, 24.8, 11.9, 11.5.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated
  3. customthe crude product was purified on silicagel column chromatography

Sources & evidence

ORD record
ord-96c91c80b9b64e9987437e19ad6f59b8
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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