Sulfuric Acid → Tert-butyl 3(rs),7-dimethyl-6-octenoate

HRID 362141

Reaktionsgleichung

Reaktionsgleichung von HRID 362141
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH3:5][CH:6]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O>ClCCl>[CH3:5][CH:6]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:15])[CH3:16])[CH2:7][C:8]([O:10][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:9]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 10402Citronellic acid

Produkt 1

HCID 22619086Tert-butyl 3(rs),7-dimethyl-6-octenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

25 ml of isobutylene were condensed at -78°C. and added to a mixture of 19.4 g (114 mmol) of 3(RS),7-dimethyl-6-octenoic acid and 1 ml of concentrated sulphuric acid in 25 ml of dichloromethane. The mixture was stirred for 24 hours under a dry ice condenser. A further 20 ml of isobutylene were added and the mixture was stirred for 24 hours under a dry ice condenser. The mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesiumsulphate and evaporated under a vacuum. The resulting oil was purified by chromatography on silica gel using ethyl acetate/hexane (1:9) for the elution. There were obtained 20.8 g of tert-butyl 3(RS),7-dimethyl-6-octenoate as a colourless oil. 1H NMR (250 MHz, CDCl3) δ: 0.9 (d, 3 H), 1.1-1.3 (m, 3 H), 1.4 (s, 9 H), 1.6 (s,3 H), 1.65, (s, 3 H), 1.8-2.2 (br m, 4 H), 5.05, (m, 1 H).

Aufarbeitung

  1. customcondensed at -78°C.
  2. stirringthe mixture was stirred for 24 hours under a dry ice condenser
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesiumsulphate
  5. customevaporated under a vacuum
  6. customThe resulting oil was purified by chromatography on silica gel
  7. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-6e4ac8bf93c84501a34ca27f3b1692cc
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866684

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