1-Bromopentane → 4-(4-Acetyl-8-hydroxy-13,13,13-trifluorotridecyl)benzoic acid

HRID 46970

Reaktionsgleichung

Reaktionsgleichung von HRID 46970
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][CH2:5][CH2:6]Br.C(Br)CCCC.ClCCCC(=O)CCCCC(F)(F)F.ClCCCC(O)CCCCC(F)(F)F.ClCCCC(OC(=O)C)CCCCC(F)(F)F.C(OC(C(C(=O)C)CCCC1C=CC(C(OCC)=O)=CC=1)=O)(C)(C)C.[C:86]([C:89](C(OC(C)(C)C)=O)([CH2:104][CH2:105][CH2:106][CH:107]([O:116]C(=O)C)CCCCC(F)(F)F)[CH2:90][CH2:91][CH2:92][C:93]1[CH:103]=[CH:102][C:96]([C:97]([O:99]CC)=[O:98])=[CH:95][CH:94]=1)(=[O:88])[CH3:87].C(C(CCCC(OC(=O)C)CCCCC(F)(F)F)CCCC1C=CC(C(OCC)=O)=CC=1)(=O)C>>[C:86]([CH:89]([CH2:104][CH2:105][CH2:106][CH:107]([OH:116])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:9])([F:8])[F:1])[CH2:90][CH2:91][CH2:92][C:93]1[CH:94]=[CH:95][C:96]([C:97]([OH:99])=[O:98])=[CH:102][CH:103]=1)(=[O:88])[CH3:87]

Komponenten

9

Edukt 8

HCID 80571-BromopentaneHCID 5803495-Bromo-1,1,1-trifluoropentaneHCID 203860351-Chloro-4-acetoxy-9,9,9-trifluorononaneHCID 20386047Ethyl 4-(4-acetyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoateHCID 20386057Ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoateHCID 203860991-Chloro-9,9,9-trifluoro-4-nonanolHCID 20386122Ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoateHCID 203861251-Chloro-9,9,9-trifluoro-4-nonanone

Produkt 1

HCID 203861244-(4-Acetyl-8-hydroxy-13,13,13-trifluorotridecyl)benzoic acid

Versuchsvorschrift

The synthesis of this compound is carried out as described in Example 1, except that in Step B(1) an equivalent amount of 1,1,1-trifluoro-5-bromopentane is substituted for amyl bromide. The product of Step B(1) thus becomes 1-chloro-9,9,9-trifluoro-4-nonanone. Subsequent steps afford in order: Step B(2), 1-chloro-9,9,9-trifluoro-4-nonanol; Step B(3), 1-chloro-4-acetoxy-9,9,9-trifluorononane; Step C, ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate; Step D, ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate (by substituting 1-chloro-4-acetoxy-9,9,9-trifluorononane for 1-chloro-4-acetoxynonane); Step E, ethyl 4-(4-acetyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate; and Step F, 4-(4-acetyl-8-hydroxy-13,13,13-trifluorotridecyl)benzoic acid, obtained as a viscous yellow oil.

Aufarbeitung

  1. customThe synthesis of this compound
  2. customSubsequent steps afford in order

Quellen und Nachweise

ORD-Eintrag
ord-adef782d75c34c7f9128e415d637ff1b
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175203

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