Methanol → HCID 66652017, compound

HRID 418969Notes

Reaction equation

HRID 418969 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[CH:12]([C:16]([OH:18])=[O:17])[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH:10]1[CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9]1.[C:26](Cl)(C)=O.CO.C(OCC)(=O)C>O>[CH3:26][O:17][C:16]([CH:12]1[CH:11]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4]2[C:13]1=[CH:14][CH:15]=[C:2]([OH:1])[CH:3]=2)=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 66652086HCID 66652086, compound

Product 1

HCID 66652017HCID 66652017, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 6-hydroxy-10-(4-hydroxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid (0.903 g, 2.67 mmol), AcCl (2 mL), and methanol (20.0 mL), and reflux under nitrogen atmosphere. After 72 hours, concentrate reaction to dryness under vacuum, add ethyl acetate and water. Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and concentrate to yield the titled compound (0.980 g, 99%) as a brown solid. 1H NMR (d-methanol): 7.15 (d, 2H, J=8.4 Hz), 7.04 (d, 1H, J=8.8 Hz), 6.91 (s, 1H), 6.77 (d, 2H, J=8.4 Hz), 6.64 (m, 1H), 4.32 (d, 1H, J=12.8 Hz), 3.58 (s, 3H), 3.45 (dd, 1H, J=12.6, 2.4 Hz), 3.34 (s, 1H), 2.52 (d, 1H, J=14.1 Hz), 1.97 (m, 1H), 1.68 (m, 2H), 1.44 (m, 2H), 1.11 (m, 3H); MS m/z 351 (M−1).

Workup

  1. concentrationconcentrate
  2. customreaction to dryness under vacuum
  3. customSeparate the organic phase
  4. washwash with brine
  5. dry with materialDry the organic phase with anhydrous sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-a32d515a92c24ca7aa1d67fe3f681a87
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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