Sodium Hydroxide → 4-[2-(Indol-2-yl)ethyloxy]benzoic acid

HRID 583659Notes

Reaction equation

HRID 583659 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1.[OH-].[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 18928558Methyl 4[2-(Indol-2-yl)ethyloxy]benzoate

Product 1

HCID 158507584-[2-(Indol-2-yl)ethyloxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ester 4-3 (150 mg, 0.51 mmol) and 1N NaOH (1.3 mL, 1.3 mmol) were combined in 10 mL MeOH. After 16 h additional 1N NaOH (5 mL, 5 mmol) was added, and 7 h later, 5 mL more 1N NaOH. After a total of 2 d the mixture was heated at 50° for 1 h, then concentrated, redissolved in H2O, washed with EtOAc, and the pH of the aqueous layer was adjusted to 1 with 20% KHSO4. This was extracted with EtOAc, and this organic layer was washed with brine, dried (MgSO4) and concentrated, providing 4-4 as a gray solid. Rf 0.48 (silica, EtOAc).

Workup

  1. custom7 h
  2. temperatureAfter a total of 2 d the mixture was heated at 50° for 1 h
  3. concentrationconcentrated
  4. dissolutionredissolved in H2O
  5. washwashed with EtOAc
  6. extractionThis was extracted with EtOAc
  7. washthis organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-34f9d5409df148f4885c167e50e17a35
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…