Chlorendic anhydride → Chroman

HRID 1248367Notes

Reaction equation

HRID 1248367 reaction equation
[C:1]12[C:10](=O)OC(=O)[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6]2.C12C(=O)O[C:18](=[O:19])[CH:13]1CCCC2.C1(=O)OC(=O)C=C1C.C12CC(CC1)C1C(OC(=O)C21)=O.ClC12C(Cl)(Cl)C(Cl)(C(Cl)=C1Cl)C1C(OC(=O)C21)=O.CC1CC2C(=O)OC(=O)C2CC=1.CC1C2CC(C=1)C1C(OC(=O)C21)=O.C12CC(C=C1)C1C(OC(=O)C21)=O>>[O:19]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:10][CH2:13][CH2:18]1

Participants

9

Reactant 8

HCID 8265Chlorendic anhydrideHCID 12012Citraconic AnhydridesHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13223826-62-0HCID 85689Hexahydrophthalic anhydrideHCID 96196Hexahydro-4,7-methano-2-benzofuran-1,3-dioneHCID 984963a,4,7,7a-Tetrahydro-5-methyl-1,3-isobenzofurandioneHCID 5201863a,4,7,7a-Tetrahydro-5-methyl-4,7-methanoisobenzofuran-1,3-dione

Product 1

HCID 136319Chroman

Procedure

The same reaction and isolation procedures as Synthesis Example 85 were followed except that 1.52 g of 1-cyclohexene-1,2-dicarboxylic anhydride, 1.54 g of cyclohexane-1,2-dicarboxylic anhydride, 1.12 g of citraconic anhydride, 1.66 g of norbornane-2,3-dicarboxylic anhydride, 3.71 g of 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic anhydride, 1.66 g of 4-methyl-4-cyclohexene-1,2-dicarboxylic anhydride or 1.78 g of 5-methyl-5-norbornene-2,3-dicarboxylic anhydride was used in lieu of 1.64 g of 5-norbornene-2,3-dicarboxylic anhydride to give the corresponding 3,4-dihydro-2H-benzopyran derivative. The results are given in Table 12. ##STR109##

Workup

  1. customThe same reaction and isolation procedures
  2. customas Synthesis Example 85

Sources & evidence

ORD record
ord-dbd59f5d046f4d6081dfd2d1561f630b
Source dataset
uspto-grants-1985_06
Patent number
US04523024

Reaction notes

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