Acetic Acid → HCID 13646822, compound

HRID 364807Notes

Reaction equation

HRID 364807 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]C)=[O:25].C(O)(=O)C.Cl.C(O)(=O)CCCC>O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7991Pentanoic AcidHCID 13646821HCID 13646821, compound

Product 1

HCID 13646822HCID 13646822, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]pentanoate (14 g., 0.0339 mole), acetic acid (100 ml) and 6N hydrochloric acid (50 ml) is stirred and refluxed for 6 hours. The mixture is poured into water (400 ml) and the product which solidifies upon standing is removed by filtration and dried. The product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml) to give 12.5 g, of 5-[6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1-inden-5-yl)oxy)pentanoic acid, m.p. 106°-108° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. customupon standing is removed by filtration
  3. customdried
  4. customThe product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml)
  5. customto give 12.5 g

Sources & evidence

ORD record
ord-28f09150da944c29a3fc6a3b688d4065
Source dataset
uspto-grants-1986_08
Patent number
US04605663

Reaction notes

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