Acetic Anhydride → 1-(4-Acetoxy-3-carboxyphenyl)-2-phenylindole

HRID 1579868Notes

Reaction equation

HRID 1579868 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2].[C:26](OC(=O)C)(=[O:28])[CH3:27].O1CCCC1>O>[C:26]([O:10][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:5][C:4]=1[C:1]([OH:3])=[O:2])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 122703211-(3-Carboxy-4-hydroxyphenyl)-2-phenylindole

Product 1

HCID 214006481-(4-Acetoxy-3-carboxyphenyl)-2-phenylindole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.25 g. (0.025 mole) of 1-(3-carboxy-4-hydroxyphenyl)-2-phenylindole and 76.5 g. (0.75 mole) of acetic anhydride was heated under reflux for 1 hour, diluted with 75 ml. of tetrahydrofuran and poured into 1 l. of water. An oil separated, and during 2 days solidified. The solid was collected and recrystallized from acetonitrile to provide 4.8 g. (52%) of colorless crystals, m.p. 178°-180°.

Workup

  1. additionA mixture of 8.25 g
  2. temperatureunder reflux for 1 hour
  3. additiondiluted with 75 ml
  4. customAn oil separated
  5. customThe solid was collected
  6. customrecrystallized from acetonitrile
  7. customto provide 4.8 g

Sources & evidence

ORD record
ord-d9f9eed095f04d199437e997cd7695ca
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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