Hydrochloric Acid → 4-(2-Methoxyethoxy)-3-methylbenzoic acid

HRID 72925

Reaktionsgleichung

Reaktionsgleichung von HRID 72925
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].C([P+](CCCC)(CCCC)CCCC)CCC.Br[CH2:31][CH2:32][O:33][CH3:34].Cl>C1COCC1>[CH3:34][O:33][CH2:32][CH2:31][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 681384-Hydroxy-3-methylbenzoic acidHCID 809722-Bromoethyl methyl etherHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Produkt 1

HCID 585513704-(2-Methoxyethoxy)-3-methylbenzoic acidAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-hydroxy-3-methyl-benzoic acid (2.0 g, 13 mmol) in THF (24 mL) was added tetrabutylphosphonium hydroxide (18 mL of 40% w/v, 26 mmol). The reaction mixture was cooled to 0° C. and then 1-bromo-2-methoxy-ethane (1.8 g, 1.2 mL, 13 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was acidified using 1M HCl and the aqueous layer was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated in vacuo to yield 4-(2-methoxyethoxy)-3-methylbenzoic acid (182 mg, 6%). ESI-MS m/z calc. 210.2. Found 209.2 (M-H)−; Retention time: 0.96 minutes (3 min run).

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d725e47a55940a89ffe32a8dd1e32ff
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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