Ethanol → 3,5-Dichloro-4-[5-(3-methylisoxazol-5-yl)pentyloxy]benzoic acid

HRID 2166466Notes

Reaction equation

HRID 2166466 reaction equation
[Cl:1][C:2]1[CH:19]=C(C#N)[CH:17]=[C:16]([Cl:22])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1.[OH-:23].[Na+].[CH2:25]([OH:27])[CH3:26]>>[Cl:1][C:2]1[CH:19]=[C:26]([CH:17]=[C:16]([Cl:22])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1)[C:25]([OH:23])=[O:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 104723405-[5-(2,6-Dichloro-4-cyanophenoxy)pentyl]-3-methylisoxazole

Product 1

HCID 148360183,5-Dichloro-4-[5-(3-methylisoxazol-5-yl)pentyloxy]benzoic acid

Procedure

A mixture of 6.11 g 5-[5-(2,6-dichloro-4-cyanophenoxy)pentyl]-3-methylisoxazole (m.p. 59°-60° C.), 75 ml 35% sodium hydroxide and 75 ml ethanol was stirred on a steam bath for several hours. The reaction mixture upon standing separated into a clear lower layer and a yellow upper layer. The latter was separated, diluted with cold water and acidified with hydrochloric acid. The resulting solid was collected and recrystallized from acetonitrile to give 5.24 g 3,5-dichloro-4-[5-(3-methylisoxazol-5-yl)pentyloxy]benzoic acid, m.p. 67°-69° C.

Workup

  1. customThe reaction mixture upon standing separated into a clear lower layer
  2. customThe latter was separated
  3. additiondiluted with cold water
  4. customThe resulting solid was collected
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ede6e08a22f14ea289c3f65ce8ba63c6
Source dataset
uspto-grants-1990_07
Patent number
US04945164

Reaction notes

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