Indole-3-Acetic Acid → Benzyl (1H-indol-3-yl)acetate

HRID 1110340Notes

Reaction equation

HRID 1110340 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.[OH-].[CH2:15]([N+](CC)(CC)C1C=CC=CC=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCC>[CH2:15]([O:12][C:11](=[O:13])[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 802Indole-3-Acetic AcidHCID 86744362HCID 86744362, compound

Product 1

HCID 19603827Benzyl (1H-indol-3-yl)acetateYield 80.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Indole 3-acetic acid 1 (9.45 g, 0.054 mol) was dissolved in methanolic benzyl diethyl anilinium hydroxide (0.54 mol) and the solvent removed in vacuo. The oily residue of the benzyl dimethyl anilinium salt was agitated with benzene, the benzene evaporated and the salt refluxed in toluene (170 ml, 1 h). Traces of unreacted acid and dimethyl aniline by-product were removed by extracting the toluene solution with water, dilute hydrochloric acid (1N) and water. The organic layer was dried over sodium sulphate and concentrated in vacuo to obtain the crude product. Final purification was obtained by crystallization in EtOAc:Hexane to give 11.52 g (80%) indole-3-acetic acid benzyl ester 13 as white crystals (melting point 71°-72° C.); IR (Nujol, cm-1); 3 400, 1, 720; 1H-NMR (CDCl3,δ): 3.8 (s, 2 H), 5.1 (s, 2 H) 6.8-8.0 (m, 1 H).

Workup

  1. customthe solvent removed in vacuo
  2. customthe benzene evaporated
  3. temperaturethe salt refluxed in toluene (170 ml, 1 h)
  4. customTraces of unreacted acid and dimethyl aniline by-product were removed
  5. extractionby extracting the toluene solution with water, dilute hydrochloric acid (1N) and water
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product
  9. customFinal purification
  10. customwas obtained by crystallization in EtOAc

Sources & evidence

ORD record
ord-fc514fc6603d4d8cbca059db91015f21
Source dataset
uspto-grants-1990_12
Patent number
US04975298

Reaction notes

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