Acetic Anhydride → 1-(4-Acetoxy-3-carboxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

HRID 1579865Notes

Reaction equation

HRID 1579865 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=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[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:4]=1[C:1]([OH:3])=[O:2])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 9967439HCID 9967439, compound

Product 1

HCID 122702751-(4-Acetoxy-3-carboxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25.0 g. (0.075 mole) of 1-(3-carboxy-4-hydroxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole and 225 g. (2.25 mole) of acetic anhydride was heated under reflux for 3 hours, diluted with 200 ml. of tetrahydrofuran, and poured into 3 l. of water. An oil separated and slowly solidified. Recrystallization from acetic acid gave a tan solid, m.p. 155°-162°.

Workup

  1. additionA mixture of 25.0 g
  2. temperatureunder reflux for 3 hours
  3. additiondiluted with 200 ml
  4. customAn oil separated
  5. customRecrystallization from acetic acid
  6. customgave a tan solid, m.p. 155°-162°

Sources & evidence

ORD record
ord-2b0aab11923946e8888f2f091ac60259
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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