Hydrochloric Acid → HCID 66699605, compound

HRID 1717792Notes

Reaction equation

HRID 1717792 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#N)=[CH:12][CH:11]=2)=[C:6]([CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2].[OH-:36].[K+].Cl.[OH2:39]>C(O)C>[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]([OH:39])=[O:36])=[CH:12][CH:11]=2)=[C:6]([CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 66699571HCID 66699571, compound

Product 1

HCID 66699605HCID 66699605, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared essentially as described in Preparation 113 employing 3-[[4-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (3.20 g, 6.79 mmol) and potassium hydroxide (7.62 g, 136 mmol) in ethanol (100 mL) and water (25 mL) at reflux for 3 days. Evaporate volatiles and acidify with 1N hydrochloric acid and extract with three portions of methylene chloride. Combine organic layers, dry (sodium sulfate) and evaporate to afford the title compound as a white solid (1.10 g, 2.24 mmol, 33%): MS (m/z): 490 (M−H).

Workup

  1. customThe title compound is prepared essentially
  2. temperatureat reflux for 3 days
  3. extractionextract with three portions of methylene chloride
  4. dry with materialCombine organic layers, dry (sodium sulfate)
  5. customevaporate

Sources & evidence

ORD record
ord-33f7c0f4409f427eb7cccaa078b3d79d
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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