Sulfuric Acid → HCID 14180572, compound

HRID 1904960Notes

Reaction equation

HRID 1904960 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[C:7](=[O:11])[CH:6]=[CH:5][C:4](=[O:12])[C:3]=2[O:2]1.[CH2:13]=[CH:14][C:15]([Cl:17])=[CH2:16].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>C(O)(=O)C.O>[Cl:17][C:15]1[CH:16]=[C:5]2[C:6](=[CH:13][CH:14]=1)[C:7](=[O:11])[C:8]1[O:9][CH2:10][CH2:1][O:2][C:3]=1[C:4]2=[O:12]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 31369ChloropreneHCID 140804552,3-Dihydro-1,4-benzodioxine-5,8-dione

Product 1

HCID 14180572HCID 14180572, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture of 2,3-ethylenedioxy-1,4-benzoquinone (17 g) and freshly distilled chloroprene (13 g) in glacial acetic acid (100 mL) was stirred at ambient temperature for 90 hours. The mixture was then diluted with additional acetic acid (500 mL) followed by the addition of a solution of sodium dichromate (40 g) and sulfuric acid (2 mL) in water (25 mL). The mixture was heated at 60° -70°C. for 2 hours, then cooled and diluted with water (500 mL). The resulting bright orange precipitate was collected and dried to yield 18.25 g of 6-chloro-2,3-ethylenedioxy-1,4-naphthoquinone, mp 279°-80° C.

Workup

  1. temperatureThe mixture was heated at 60° -70°C. for 2 hours
  2. temperaturecooled
  3. customThe resulting bright orange precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-26d9489be7e54a978c1255c7e64210fd
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

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