Sulfamic Acid → 3-Cyclopentyloxy-4-benzyloxybenzoic acid

HRID 1383517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383517
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)([OH:25])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:18]1([O:17][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13]([OH:25])=[O:14])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 3

HCID 5987Sulfamic Acid2×HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehydeHCID 23668197Sodium Chlorite2×

Produkt 1

HCID 211879313-Cyclopentyloxy-4-benzyloxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A rapidly stirred solution of 4-benzyloxy-3-cyclopentyloxybenzaldehyde (10.5 g; that is prepared as described in Reference Example 37) in glacial acetic acid (100 mL) is treated with sulfamic acid (4.85 g) and stirred at room temperature for 10 minutes. The solution is then cooled in an ice bath and treated with a solution of sodium chlorite (4.2 g) in water (100 mL) during 15 minutes at 13-15° C. During the addition a white precipitate forms and, because stirring becomes difficult, a further quantity of glacial acetic acid (60 mL) is added. After warming to room temperature, the solution is stirred for a further 6 hours and further quantities of sodium chlorite (1.6 g) and sulfamic acid (1.7 g) are added. The mixture is poured onto water and the resulting solid is filtered off and dried, to give 3-cyclopentyloxy-4-benzyloxybenzoic acid (10 g).

Aufarbeitung

  1. customthat is prepared
  2. temperatureThe solution is then cooled in an ice bath
  3. additionDuring the addition a white precipitate forms
  4. stirringbecause stirring
  5. temperatureAfter warming to room temperature
  6. stirringthe solution is stirred for a further 6 hours
  7. additionThe mixture is poured onto water
  8. filtrationthe resulting solid is filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a3660dab9128479fb27b12b4c2b1abad
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255326B1

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