Water → [2,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxin-6-yl]methanol

HRID 224388Notes

Reaction equation

HRID 224388 reaction equation
[Cl:1][C:2]([Cl:23])([Cl:22])[CH:3]1[O:8][CH:7]([C:9]([Cl:12])([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17](OCC)=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>CCOCC>[OH:18][CH2:17][C:14]1[CH:15]=[CH:16][C:5]2[O:4][CH:3]([C:2]([Cl:1])([Cl:22])[Cl:23])[O:8][CH:7]([C:9]([Cl:12])([Cl:11])[Cl:10])[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23332965HCID 23332965, compound

Product 1

HCID 23332968[2,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxin-6-yl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxylate (2.0 g.) in anhydrous ether (25 ml.) was added at room temperature during 20 minutes to a suspension of lithium aluminium hydride (0.2 g.) in anhydrous ether (25 ml.). The mixture was stirred for 1 hour, then ethyl acetate (5 ml.) was added, followed by water (10 ml.). The mixture was filtered, and the ether layer of the filtrate was separated. The aqueous phase was extracted with ether (3×10 ml.), the combined extracts were dried, and the solvent was evaporated. The residue was crystallised from ethanol to give 6-hydroxymethyl-2,4-bis(trichloromethyl)benzo[1,3]dioxin, m.p. 134°-136° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe ether layer of the filtrate was separated
  3. extractionThe aqueous phase was extracted with ether (3×10 ml.)
  4. customthe combined extracts were dried
  5. customthe solvent was evaporated
  6. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-cb836e190bc84a4ebd3aa1b1f8198efb
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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