Ethyl Acetate → Pentachlorophenol

HRID 329244Notes

Reaction equation

HRID 329244 reaction equation
FC1(F)C(Cl)=C(Cl)C(F)(F)C(Cl)=C1Cl.FF.F[C:18]1(F)[C:23]([Cl:24])=[C:22]([Cl:25])[C:21]([Cl:27])(F)[C:20]([Cl:28])=[C:19]1[Cl:29].FC1C(Cl)(F)C(Cl)(F)C(Cl)=C(Cl)C=1Cl.CC(=O)[O:47]CC>>[Cl:24][C:23]1[C:18]([OH:47])=[C:19]([Cl:29])[C:20]([Cl:28])=[C:21]([Cl:27])[C:22]=1[Cl:25]

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 24524FluorineHCID 21439202HCID 21439202, compoundHCID 21439203HCID 21439203, compoundHCID 21439211HCID 21439211, compound

Product 1

HCID 992Pentachlorophenol

Procedure

In run A two principal product fractions are obtained: (1) 60.3 g, bp 91°-97° /31 mm, mp 30°; (2) 18.6 g, semisolid residue. Fraction (1) was identified as 1,1,4,4-tetrafluorotetrachloro-2,5-cyclohexadiene by comparison of its IR and MS data with those of a known sample of the compound (Hasek et al., Jour. Am. Chem. Soc., vol. 82, p. 543, 1960) Fraction (2) was indicated by fluorine NMR, IR, VPC and EA analyses to be a mixture of isomeric 1,1,4-trifluoropentachloro-2,5-cyclohexadiene and 1,5,6-trifluoropentachloro-1,3-cyclohexadiene.

Workup

  1. customIn run A two principal product fractions are obtained

Sources & evidence

ORD record
ord-178a1e808dd449bf9658c0c98ccad2a8
Source dataset
uspto-grants-1977_04
Patent number
US04020112

Reaction notes

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