Sodium Hydroxide → HCID 14097620, compound

HRID 1762181Notes

Reaction equation

HRID 1762181 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14097617HCID 14097617, compound

Product 1

HCID 14097620HCID 14097620, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ten grams of methyl 4-[2-(4-chlorobenzamido)ethoxy]benzoate was dissolved in 100 ml of hot ethanol. A solution of 2.4 g of sodium hydroxide in 20 ml of water was added to the above ethanolic solution and the mixture was heated to reflux for 2 hours. The reaction solution was concentrated in vacuo, 100 ml of water was added to the residue, the mixture was neutralized with 10% hydrochloric acid, crystals separated out were collected by filtration, washed with water, dried and recrystallised from ethanol to give 8.4 g (yield: 87%) of crystalline product. M.p. 219°-220° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction solution was concentrated in vacuo, 100 ml of water
  4. additionwas added to the residue
  5. customseparated out
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-15daeabb6eb241a8a73d10e72b9ecc38
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

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