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1-Chloro-1,1,3,3,3-pentafluoro-2-propanone → 1,1,1,3,3-Pentafluoro-2-(4-ethoxyphenyl)-3-chloropropan-2-ol

HRID 483727
Notes
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Reaction equation

HRID 483727 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[Cl:10][C:11]([F:19])([F:18])[C:12]([C:14]([F:17])([F:16])[F:15])=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)(Cl)Cl>[F:15][C:14]([F:17])([F:16])[C:12]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1)([OH:13])[C:11]([F:19])([F:18])[Cl:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 66011-Chloro-1,1,3,3,3-pentafluoro-2-propanoneHCID 7674PhenetoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 138807621,1,1,3,3-Pentafluoro-2-(4-ethoxyphenyl)-3-chloropropan-2-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethoxybenzene (67 g), chloropentafluoroacetone (100 g) and aluminium chloride (7 g) was charged to a Hastalloy lined cell at -78° C, the cell sealed and heated to 120° C for 8 hours. After cooling and venting, the residue was taken up in chloroform and filtered through silica gel. After removal of the solvent by evaporation the residual solid was recrystallised from n-hexane to yield several crops of 1,1,1,3,3-pentafluoro-2-(4-ethoxyphenyl)-3-chloropropan-2-ol. (Total 70 g) mp. 84°-86° C.

Workup

  1. additionwas charged to a Hastalloy
  2. customat -78° C
  3. customthe cell sealed
  4. temperatureAfter cooling
  5. filtrationfiltered through silica gel
  6. customAfter removal of the solvent
  7. customby evaporation the residual solid
  8. customwas recrystallised from n-hexane

Sources & evidence

ORD record
ord-dcdfcf8fab2f45d09b224096d3eb9f89
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05225607

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes