1-Bromopentane → 4-(4-Acetyl-8-hydroxy-12,12-dimethyltridecyl)benzoic acid

HRID 26601

Reaktionsgleichung

Reaktionsgleichung von HRID 26601
Br[CH2:2][CH2:3][CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(Br)CCCC.ClC[CH2:17][CH2:18][C:19](=[O:27])CCCC(C)(C)C.ClCCCC(O)CCCC(C)(C)C.ClCCCC(OC(=O)C)CCCC(C)(C)C.C(O[C:62]([CH:64]([C:79](=[O:81])[CH3:80])[CH2:65][CH2:66][CH2:67][C:68]1[CH:78]=[CH:77][C:71]([C:72]([O:74]CC)=[O:73])=[CH:70][CH:69]=1)=O)(C)(C)C.C(C(C(OC(C)(C)C)=O)(CCCC(OC(=O)C)CCCC(C)(C)C)CCCC1C=CC(C(OCC)=O)=CC=1)(=O)C.C(C(CCCC(OC(=O)C)CCCC(C)(C)C)CCCC1C=CC(C(OCC)=O)=CC=1)(=O)C>>[C:79]([CH:64]([CH2:62][CH2:17][CH2:18][CH:19]([OH:27])[CH2:2][CH2:3][CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:65][CH2:66][CH2:67][C:68]1[CH:69]=[CH:70][C:71]([C:72]([OH:74])=[O:73])=[CH:77][CH:78]=1)(=[O:81])[CH3:80]

Komponenten

9

Edukt 8

HCID 80571-BromopentaneHCID 157525741-Bromo-4,4-dimethylpentaneHCID 203860361-Chloro-4-acetoxy-8,8-dimethylnonaneHCID 20386053Ethyl 4-(4-acetyl-8-acetoxy-12,12-dimethyltridecyl)benzoateHCID 20386057Ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoateHCID 20386070Ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-12,12-dimethyltridecyl)benzoateHCID 203860781-Chloro-8,8-dimethyl-4-nonanolHCID 203860981-Chloro-8,8-dimethyl-4-nonanone

Produkt 1

HCID 203860774-(4-Acetyl-8-hydroxy-12,12-dimethyltridecyl)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-bromo-4,4-dimethylpentane in substituted for amyl bromide. The product of Step B(1) thus becomes 1-chloro-8,8-dimethyl-4-nonanone. Subsequent steps afford in order: Step B(2), 1-chloro-8,8-dimethyl-4-nonanol; Step B(3), 1-chloro-4-acetoxy-8,8-dimethylnonane; Step C, ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate (unchanged from Example 1); Step D, ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-12,12-dimethyltridecyl)-benzoate (by substituting 1-chloro-4-acetoxy-8,8-dimethylnonane for 1-chloro-4-acetoxynonane); Step E, ethyl 4-(4-acetyl-8-acetoxy-12,12-dimethyltridecyl)benzoate; and Step F, 4-(4-acetyl-8-hydroxy-12,12-dimethyltridecyl)benzoic acid, obtained as a viscous yellowish oil.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1141f0117e9948758d6da2b9796bfdc3
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04150235

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