Acetic Acid → 3-(4-Acetoxy-3-carboxyphenyl)-1-acetyl-4,5-dihydro-2-phenylbenz[e]indole

HRID 1579881Notes

Reaction equation

HRID 1579881 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[CH:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2].[C:30](OC(=O)C)(=[O:32])[CH3:31].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:48](O)(=[O:50])[CH3:49]>>[C:30]([O:10][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[C:19]3[CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[C:13]([C:48](=[O:50])[CH3:49])=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][C:4]=1[C:1]([OH:3])=[O:2])(=[O:32])[CH3:31]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 40821Fendosal

Product 1

HCID 215696103-(4-Acetoxy-3-carboxyphenyl)-1-acetyl-4,5-dihydro-2-phenylbenz[e]indoleYield 16%

Procedure

A mixture of 1.25 g. (0.0033 mole) of 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole, 1 ml. of acetic anhydride, 10 ml. of glacial acetic acid, and 0.1 g. of p-toluenesulfonic acid was stirred at room termperature under nitrogen for 6 days. The solid which separated was collected, washed with acetic acid and petroleum ether, dried and recrystallized from methanol to provide 0.23 g (16%) of 3-(4-acetoxy-3-carboxyphenyl)-1-acetyl-4,5-dihydro-2-phenylbenz[e]indole. Concentration of the mother liquor, followed by recrystallization of the residue from ethanol-water, gave 0.25 g. (18%) of crystals, m.p. 223°-226°.

Workup

  1. additionA mixture of 1.25 g
  2. customThe solid which separated
  3. customwas collected
  4. washwashed with acetic acid and petroleum ether
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c16f98fcffca4e81afa38c521bfda3c0
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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