4-Chlororesorcinol → 2',4,5,6,7,7'-hexachloro-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

HRID 41612

Reaction equation

HRID 41612 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=O)[O:10][C:8](=[O:9])[C:7]=12.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([OH:21])=[CH:19][C:18]=1[OH:24]>CN(C=O)C.O>[Cl:16][C:17]1[C:18]([OH:24])=[CH:19][C:20]2[O:21][C:20]3[C:22](=[CH:23][C:17]([Cl:16])=[C:18]([OH:24])[CH:19]=3)[C:11]3([C:6]4[C:7](=[C:2]([Cl:1])[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]=4[Cl:13])[C:8](=[O:9])[O:10]3)[C:22]=2[CH:23]=1

Participants

4

Reactant 2

HCID 17314-ChlororesorcinolHCID 8326Tetrachlorophthalic anhydride

Product 1

HCID 101871262',4,5,6,7,7'-hexachloro-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-oneYield 98.1%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

Treatment of tetrachlorophthalic anhydride (5 g, 17.49 mmol) and 4-chlororesorcinol (6.32 g, 43.73 mmol), according to the procedure described in Example 1 Step 1, provided 10.31 g of crude product. Suspension of a 9.25 g portion of this in DMF:water (1:1) followed by filtration, provided 9.70 g (2:1 DMF complex 17.16 mmol, 92.3% yield) of 2′,4,5,6,7,7′-hexachloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one that was isolated as an orange solid. 1H NMR (300 MHz; DMSO d6) δ 11.13 (S, 2H), 7.31 (s, 2H), 6.89 (s, 2H).

Workup

  1. customprovided 10.31 g of crude product
  2. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-2bf38e5f65294e9b907da17a98f437f1
Source dataset
uspto-grants-2013_09
Patent number
US08530675B2

Linked notes

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