Sodium Hydroxide → HCID 23508809, compound

HRID 1884271Notes

Reaction equation

HRID 1884271 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:36])[CH:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)=[O:14])=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][CH:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:27][CH:26]=2)[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:37])=[O:2])=[CH:5][CH:6]=2)=[O:36])=[CH:20][CH:19]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483317HCID 67483317, compound

Product 1

HCID 23508809HCID 23508809, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[4-(4-tert-Butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoic acid methyl ester (13.9 g, 27.2 mmol) was suspended in ethanol (120 mL, 96%) and added sodium hydroxide (4N, 27,2 mL). After 4½ h the reaction was evaporated to dryness. The residue was added water (200 mL) and hydrochloric acid (4N, 30 mL) to pH 1-2 causing precipitation. The mixture was stirred for ½ h. The precipitate was filtered, washed carefully with water, and dried the night over at 40° C. in vacuo. The residue was crystallised from methanol and water to afford 4-[4-(4-tert-butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoic acid (10.4 g).

Workup

  1. customAfter 4½ h the reaction was evaporated to dryness
  2. additionThe residue was added water (200 mL) and hydrochloric acid (4N, 30 mL) to pH 1-2
  3. customprecipitation
  4. filtrationThe precipitate was filtered
  5. washwashed carefully with water
  6. customdried the night over at 40° C. in vacuo
  7. customThe residue was crystallised from methanol and water

Sources & evidence

ORD record
ord-f89f08cf7a9b4b1fab7fb3e649aec28d
Source dataset
uspto-grants-2004_07
Patent number
US06762318B2

Reaction notes

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