Sodium Hydroxide → HCID 13092098, compound

HRID 485171Notes

Reaction equation

HRID 485171 reaction equation
[C:1]([NH:4][C:5]1[C:6]([CH:24]=[O:25])=[C:7]([CH:21]=[CH:22][CH:23]=1)[O:8][CH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([NH:4][C:5]1[C:6]([CH:24]=[O:25])=[C:7]([CH:21]=[CH:22][CH:23]=1)[O:8][CH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13092097HCID 13092097, compound

Product 1

HCID 13092098HCID 13092098, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Ethyl 4-(3-acetylamino-2-formylphenoxymethyl)benzoate (0.45 g, 0.00132 N) was suspended in 95% ethanol (10 ml) with stirring and treated with 1N sodium hydroxide solution (1.32 ml) over 1 hour. The mixture was then diluted with water (3 ml) and stirred at room temperature overnight. A further 15 ml of water was added and the mixture stirred at room temperature (4 hr). The mixture was then extracted with ethyl acetate and the aqueous phase acidified with concentrated hydrochloric acid with cooling. The precipitated solid was filtered off, washed well with water, and recrystallised from ethanol to give 4-(3-acetylamino-2-formylphenoxymethyl)benzoic acid, m.p. 242°-244° C. (dec.) (Found: C, 65.27; H, 4.93; M, 4.23%. C17H15NO5 requires C, 65.17; H, 4.83; N, 4.47%).

Workup

  1. stirringstirred at room temperature overnight
  2. stirringthe mixture stirred at room temperature (4 hr)
  3. extractionThe mixture was then extracted with ethyl acetate
  4. temperaturewith cooling
  5. filtrationThe precipitated solid was filtered off
  6. washwashed well with water
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-0089247d5dd7431f8e0307c1666a3364
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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