Hydrochloric Acid → 4'-Methoxy(1,1'-biphenyl)-4-carboxylic acid

HRID 1275411

Reaktionsgleichung

Reaktionsgleichung von HRID 1275411
BrBr.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:5])C.S([O-])([O-])=[O:21].[Na+].[Na+].Cl>O.O1CCOCC1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:3]([OH:5])=[O:21])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 24437Sodium SulfiteHCID 3015571-(4'-Methoxy(1,1'-biphenyl)-4-yl)ethanone

Produkt 1

HCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acidAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 64.7 g (1.61 mol) of soda in 560 ml water is prepared at 0° C. 69.9 g (0.44 mol) of bromine then 260 ml of 1,4-dioxane are added successively. A yellow solution is obtained which is cooled down to 0° C. and which is added over 10 minutes, without exceeding 10° C., to a suspension of 28 g (0.12 mol) of 4'-acetyl-4-methoxybiphenyl in a mixture of 750 ml of 1,4-dioxane and 510 ml water. The reaction medium is agitated for 1 hour at approximately 20° C., a solution of 15.5 g of sodium sulphite in 160 ml water is added and taken to reflux for 10 minutes. 76 ml of concentrated hydrochloric acid is added and the reaction medium is left under agitation whilst being cooled down, for 1 hour. After drying, washing with water and drying at 50° C., 25.5 g of 4'-methoxy-4-biphenyl carboxylic acid is obtained in the form of a white powder (yield: 93%).

Aufarbeitung

  1. customA yellow solution is obtained which
  2. additionwhich is added over 10 minutes
  3. temperatureto reflux for 10 minutes
  4. waitthe reaction medium is left under agitation
  5. temperaturewhilst being cooled down, for 1 hour
  6. customAfter drying
  7. washwashing with water
  8. customdrying at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-61b8de6292bf42d3a801a6f444ab5ebe
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06160157

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