Thionyl Chloride → HCID 21430653, compound

HRID 437200Notes

Reaction equation

HRID 437200 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH:19](O)[CH2:20][O:21][C:22]3[C:27]4[C:28](=[O:37])[CH:29]=[C:30]([C:32]([O:34]CC)=[O:33])[O:31][C:26]=4[CH:25]=[CH:24][CH:23]=3)[C:9]=2[C:10](=[O:12])[CH:11]=1)=[O:5])C.S(Cl)([Cl:41])=O>ClCCCl>[Cl:41][CH:19]([CH2:20][O:21][C:22]1[C:27]2[C:28](=[O:37])[CH:29]=[C:30]([C:32]([OH:34])=[O:33])[O:31][C:26]=2[CH:25]=[CH:24][CH:23]=1)[CH2:18][O:17][C:13]1[C:9]2[C:10](=[O:12])[CH:11]=[C:6]([C:4]([OH:3])=[O:5])[O:7][C:8]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 204318Cromophene

Product 1

HCID 21430653HCID 21430653, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 24.5 parts of 5,5'-[(2-hydroxytrimethylene)dioxy]bis [4-oxo-4H-1-benzopyran-2-carboxylic acid] diethyl ester and 47.6 parts of thionyl chloride in 40 parts of dry 1,2-dichloroethane was refluxed for 16 hours. The solvent was then evaporated, the residue was triturated with petrol and the resulting solid was crystallized from ethanol to give 15.6 parts of 5,5'-[(2-chlorotrimethylene)dioxy]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid], diethyl ester as white crystals m.p. 144°-144.5° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was then evaporated
  3. customthe residue was triturated with petrol
  4. customthe resulting solid was crystallized from ethanol

Sources & evidence

ORD record
ord-cd0b45c5018846c6a64979c86d933310
Source dataset
uspto-grants-1977_06
Patent number
US04029802

Reaction notes

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