3-Hydroxybenzyl alcohol → 2-(3-Hydroxymethylphenoxy)phenylacetic acid

HRID 129594

Reaktionsgleichung

Reaktionsgleichung von HRID 129594
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25].Cl>O.CN(C=O)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25]

Komponenten

7

Edukt 4

HCID 1023-Hydroxybenzyl alcoholHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 877542-Bromophenylacetic acid

Produkt 1

HCID 151257372-(3-Hydroxymethylphenoxy)phenylacetic acidAusbeute 130,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3-Hydroxybenzyl alcohol (31.0 g) was ground finely and stirred with potassium carbonate (34.6 g), 2-bromophenylacetic acid (26.9 g) and cuprous chloride (large spatula full) under nitrogen. The mixture was warmed to 140° C., and stirred vigorously for 31/2 hours. DMF (60 ml) was then added to the stirred melt and the solution was allowed to cool, poured into water and acidified with dilute hydrochloric acid. The aqueous layer was extracted with ether, and the ether extracts were washed with water, dried and evaporated to give 2-(3-hydroxymethylphenoxy)phenylacetic acid as a brown oil (42.03 g) which was used without further purification.

Aufarbeitung

  1. temperatureto cool
  2. extractionThe aqueous layer was extracted with ether
  3. washthe ether extracts were washed with water
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ccde36f6580d4ba39e2922e675ab5822
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468857

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