Hydrochloric Acid → 3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid

HRID 1818482Notes

Reaction equation

HRID 1818482 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:25])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#N)=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[OH-:32].[K+].C(O)C.Cl.[OH2:38]>>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:25])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]([OH:38])=[O:32])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962Water2×HCID 14797Potassium HydroxideHCID 666995493-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile

Product 1

HCID 578844973-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acidYield 75%

Procedure

A mixture of 3-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile (320 mg, 0.772 mmol), potassium hydroxide (1.0 g, 17.85 mmol), water (2 mL), and ethanol (10 mL) is stirred at reflux overnight. The reaction is cooled, the pH is adjusted to 2 with aqueous 5N hydrochloric acid and diluted with water (50 mL). The product is extracted with ethyl acetate (2×50 mL). The combined extracts are washed with water (50 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound (250 mg, 75%) as a white powder. 1H NMR (DMSO-d6) δ 12.85 (bs, 2H), 7.98 (s, 1H), 7.80 (d, 2H), 7.64 (d, 1H), 7.38-7.47 (m, 5H), 6.72 (d, 1H), 6.05 (d, 1H), 5.81 (d, 1H), 5.23 (s, 2H), 2.56-2.61 (m, 5H), 1.45-1.53 (m, 2H), 0.87 (t, 3H). LCMS 433 M−1.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction is cooled
  3. extractionThe product is extracted with ethyl acetate (2×50 mL)
  4. washThe combined extracts are washed with water (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f775f1b8217f4765b64ccabdc9e4188a
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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