Hydrochloric Acid → 3-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid

HRID 1717784Notes

Reaction equation

HRID 1717784 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]([Cl: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]([Cl:34])[C:5]=1[OH:35])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 578844993-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

Product 1

HCID 666994513-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a solution of 3-[[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (10.00 g, 20.33 mmol) and potassium hydroxide (22.81 g, 406.5 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 CH2Cl2 (3×). Combine organic layers, dry (sodium sulfatesodium sulfate) and evaporate to afford the title compound as a white solid (10.00 g, 19.57 mmol, 96%): MS (m/z): 510 (M−H).

Workup

  1. temperatureat reflux for 3 days
  2. extractionextract with CH2Cl2 (3×)
  3. dry with materialCombine organic layers, dry (sodium sulfatesodium sulfate)
  4. customevaporate

Sources & evidence

ORD record
ord-f8e81a0e372c4dd782e9b2db8714692c
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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