Hydrochloric Acid → 4-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoic Acid

HRID 2241031Notes

Reaction equation

HRID 2241031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68506769Ethyl 4-({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoate

Product 1

HCID 111777504-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoic AcidYield 84.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The hydrolysis procedure described for 11 (example 5, step 3) was used. A solution of ethyl 4-({4-[(4-fluorophenyl) (3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy) butanoate) (12) (0.665 g, 1.47 mmol) in THF/EtOH (1:1, 10 mL) was treated with 1 N NaOH (5 mL, excess) at 70° C. for 1 h. The reaction mixture was cooled and poured into 20% aqueous HCl (40 mL). Standard work-up followed by purification afforded 0.525 g (84%) of the title compound 13 as a white foam. 1H NMR (300 MHz, DMSO-d6): δ12.13 (br s, 1H), 7.15 (d, J=6.6 Hz, 2H), 7.12 (d, J=9.6 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 3.94 (t, J=6.3 Hz, 2H), 2.37 (t, J=7.2 Hz, 2H), 1.93 (s, J=2H), 1.89 (s, 2H), 1.76 (quintet, J=6.3 Hz, 2H), 1.27 (s, 2H), 0.89 (s, 12H). LCMS (ESI): m/z 423 (M−H)−. Anal. Calcd for C27H33FO3, C, 76.39, H, 7.83, F, 4.47. Found: C, 76.30, H, 7.90, F, 4.52.

Workup

  1. customThe hydrolysis procedure
  2. temperatureThe reaction mixture was cooled
  3. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-17ed2a4616af4ae6b3fa46e3e2d3360a
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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