Sodium Hydroxide → HCID 14459384, compound

HRID 1904422Notes

Reaction equation

HRID 1904422 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5]/[C:6](/[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[CH:7]\[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5]/[C:6](/[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[CH:7]\[C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20039091HCID 20039091, compound

Product 1

HCID 14459384HCID 14459384, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing ethyl 4-[6,6-dimethyl-2-(1H-imidazol-1-ylmethyl)-1-heptenyl]benzoate (prepared as in Example 14; 0.7 g, 0.0017 mol) in ethanol (10 ml ) was treated with aqueous sodium hydroxide (3.5 ml of 1M). The resulting mixture was stirred at room temperature for 5 hours after which time the solvent was evaporated off under reduced pressure and the resulting residue was dissolved in water (100 ml) and washed with ethyl acetate. The aqueous solution was acidified to pH 6.5 with hydrochloric acid and extracted with ethyl acetate (3×150 ml). The extracts were combined, dried over sodium sulfate, and the solvent was evaporated off under reduced pressure to yield a crude product. The crude product was recrystallised from dichloromethane-pentane to yield 4-[6,6-dimethyl-2-(1H-imidazol-1-ylmethyl)-1E-heptenyl]benzoic acid as a colorless, crystalline solid, having a melting point of 190°-192° C. and the following structural characteristics:

Workup

  1. customwas evaporated off under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water (100 ml)
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated off under reduced pressure
  7. customto yield a crude product
  8. customThe crude product was recrystallised from dichloromethane-pentane

Sources & evidence

ORD record
ord-21ab82b0a93545aeb0d6e9574fb0532d
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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