Sodium Hydroxide → Tucaresol

HRID 485164

Reaction equation

HRID 485164 reaction equation
[CH:1]([C:3]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][CH:8]=1)=[O:2].[OH-].[Na+]>C(O)C.O>[CH:1]([C:3]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9861133Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate

Product 1

HCID 55223Tucaresol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate (0.6 g. 0.002 M) was suspended in 95% ethanol (5 ml) and 1 N sodium hydroxide solution (5 ml) and stirred at room temperature (2.5 hr). The yellow solution was diluted with water, extracted with ethyl acetate, and acidified with concentrated hydrochloric acid. The precipitated solid was filtered off, washed well with water, and recrystallised from 95% ethanol to give 4-(2-formyl-3-hydroxyphenoxymethyl) benzoic acid, m.p. 239°-240° C. (Found: C. 65.99; H, 4.29. C15H12O5 requires C, 66.17; H, 4.44%).

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationThe precipitated solid was filtered off
  3. washwashed well with water
  4. customrecrystallised from 95% ethanol

Sources & evidence

ORD record
ord-ff35f5f0f91c472d83d1af4b07930a86
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Linked notes

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