Triethylamine → HCID 15915436, compound

HRID 926224Notes

Reaction equation

HRID 926224 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[C:3]=1[OH:14].CCN(CC)CC>CCO.[Pd]>[CH3:12][C:11]1[CH:2]=[C:3]([OH:14])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:13])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 89676548HCID 89676548, compound

Product 1

HCID 15915436HCID 15915436, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-bromo-3,6-dimethylnaphthalen-1-ol (31.9 g, 127 mmol) in EtOH (1.3 L) was treated with Et3N (26.6 mL, 191 mmol) at room temperature. Pd/C (13.5 g, 12.7 mmol, 10% wt on C) was added in one portion and the atmosphere replaced with H2. The reaction was left under balloon pressure of H2 for 6 hours. After replacing the atmosphere with air, Celite (20 g) was added and the slurry stirred for 15 minutes before filtering the solution through a pad of Celite. The volatiles were removed in vacuo, and the residue was taken up in EtOAc/water (250 mL each). The organics were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting residue was purified on Isco silica gel column chromatography (0-35% EtOAc/hex) to afford 3,6-dimethylnaphthalen-1-ol. LCMS-ESI+ (m/z): [M+H]+ calcd for C12H13O: 173.1. found: 173.4.

Workup

  1. additionwas added
  2. filtrationbefore filtering the solution through a pad of Celite
  3. customThe volatiles were removed in vacuo
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified on Isco silica gel column chromatography (0-35% EtOAc/hex)

Sources & evidence

ORD record
ord-70afb94b6bee41799a0ada42ac08a415
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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