Sodium Hydroxide → HCID 22494663, compound

HRID 1816683Notes

Reaction equation

HRID 1816683 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[N:18]=2)=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)[N:18]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22494725HCID 22494725, compound

Product 1

HCID 22494663HCID 22494663, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 4-[5-[4-(7-methoxy-n-heptyloxy)phenyl]-1,2,4-oxadiazol-3-yl]benzoate (5.4 g) and 10% sodium hydroxide aqueous solution (15 ml) in ethanol (60 ml) and tetrahydrofuran (30 ml) was stirred at 60-70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and water added to the residue and adjusted to pH 1 using hydrochloric acid. The precipitates were collected by filtration, washed with water and dried in vacuo to give 4-[5-[4-(7-methoxy-n-heptyloxy)phenyl]-1,2,4-oxadiazol-3-yl]benzoic acid (4.4 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionadded to the residue
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d7d61fdce988480ea3f744ae9dbfe076
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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