Methanol → Methyl 3-cyclopentyloxy-4-benzyloxybenzoate

HRID 1489718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489718
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([OH:12])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:29]O>>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]([O:12][CH3:29])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 211879313-Cyclopentyloxy-4-benzyloxybenzoic acid

Produkt 1

HCID 21187943Methyl 3-cyclopentyloxy-4-benzyloxybenzoate

Versuchsvorschrift

A solution of 3-cyclopentyloxy-4-benzyloxybenzoic acid (5.1 g; that is prepared as described in Reference Example 38) in methanol (150 mL) and concentrated sulfuric acid (1 mL) is heated at reflux for 6 hours, and then it is cooled and concentrated in vacuo. The resulting residue is treated with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate solution (50 mL). The organic layer is collected, dried and evaporated. The resulting oil is subjected to flash chromatography on silica gel, using a mixture of ethyl acetate and pentane (1:4 v/v) as eluent, to give methyl 3-cyclopentyloxy-4-benzyloxybenzoate (4.8 g), in the form of a white solid, m.p. 58°-59° C.

Aufarbeitung

  1. customthat is prepared
  2. temperatureat reflux for 6 hours
  3. temperatureit is cooled
  4. concentrationconcentrated in vacuo
  5. additionThe resulting residue is treated with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  6. customThe organic layer is collected
  7. customdried
  8. customevaporated
  9. additiona mixture of ethyl acetate and pentane (1:4 v/v) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-db285b4beb0044e2a247e7f8bed333cc
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05679696

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