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Iodoacetic Acid → [(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid

HRID 223803
Notes
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Reaction equation

HRID 223803 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([OH:16])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:17][CH3:18])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:19])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.I[CH2:32][C:33]([OH:35])=[O:34]>O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:32][C:33]([OH:35])=[O:34])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:17][CH3:18])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:19])[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5240Iodoacetic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 128069355,6-dichloro-9a-ethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 12806939[(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
50 °C

Procedure

5,6-Dichloro-9a-ethyl-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one, (Example 1, Step C) (15 gm., 0.048 mole), potassium carbonate (13.3 gm., 0.096 mole), dimethylformamide (100 ml.) and iodoacetic acid (10.6 gm., 0.057 mole) is stirred at room temperature for 24 hours. The reaction mixture is poured into water (150 ml.), stirred, warmed to 50° C., filtered and the filtrate acidified with 6 N hydrochloric acid to obtain [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid, which after recrystallization from acetic acid, melts at 237° C.-238° C.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-68a1c8086cfb4b6e8c568bb8f6c83c13
Source dataset
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04356313

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes