Sulfuric Acid → HCID 23332930, compound

HRID 224403Notes

Reaction equation

HRID 224403 reaction equation
[Cl:1][C:2]([Cl:20])([Cl:19])[CH:3]1[O:8][CH:7]([C:9]([Cl:12])([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:31](OC)=[O:32].S(=O)(=O)(O)O>C(OCC)C>[CH:31]([O:18][CH2:17][C:14]1[CH:15]=[CH:16][C:5]2[O:4][CH:3]([C:2]([Cl:1])([Cl:19])[Cl:20])[O:8][CH:7]([C:9]([Cl:12])([Cl:10])[Cl:11])[C:6]=2[CH:13]=1)=[O:32]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7865Methyl formateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 233329222,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-carbaldehyde

Product 1

HCID 23332930HCID 23332930, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxaldehyde (1.0 g.) in diethylether (10 ml.) was added to a mixture of aluminium chloride (1.17 g.) and lithium aluminium hydride (0.95 g.) in diethyl ether (15 ml.). A vigorous reaction was observed during this addition, the mixture was stirred for 11/2 hours, and then a solution of methyl formate (5 ml.) in diethyl ether (20 ml.) was added at 0° C. The reaction mixture was allowed to reach ambient temperature, and 20% sulphuric acid (25 ml.) was added. The organic layer was separated, dried, and concentrated under reduced pressure to give an oily product which readily solidified on trituration with petroleum ether (b.p. 60°-80° C.) to give 6-formyloxymethyl-2,4-bis(trichloromethyl)benzo[1,3]dioxin, m.p. 75°-77° C.

Workup

  1. customA vigorous reaction
  2. additionwas observed during this addition
  3. customto reach ambient temperature
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give an oily product which

Sources & evidence

ORD record
ord-a0a7aa989eeb419a96d3e05e6a1ede4c
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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