Hydrochloric Acid → 4-Acetoxymethylindole

HRID 569077

Reaction equation

HRID 569077 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:12](OC(=O)C)(=[O:14])[CH3:13].Cl.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.O.CCOCC>[C:12]([O:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2)(=[O:14])[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 27734571H-indol-4-ylmethanol

Product 1

HCID 201323834-Acetoxymethylindole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Hydroxymethylindole (17 g) is heated in pyridine (12 ml) with acetic anhydride (11.9 ml) for three hours on the steam bath. After dilution with ether, the reaction mixture is first shaken out with 1N hydrochloric acid, then with saturated sodium bicarbonate solution and finally with water. The ether solution is evaporated. 20 g of 4-acetoxymethylindole remains.

Workup

  1. customThe ether solution is evaporated

Sources & evidence

ORD record
ord-f5a6e312d5b741aaa43bf70079b5d383
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Linked notes

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