Barium hydroxide, monohydrate → 3-Hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid

HRID 403175

Reaktionsgleichung

Reaktionsgleichung von HRID 403175
C[O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[O:9][CH2:10][CH:11]([CH2:13][OH:14])[O:12][C:7]=2[C:6]=1[CH3:17])=[O:4].O.[OH-].[Ba+2].[OH-]>CO>[OH:14][CH2:13][CH:11]1[CH2:10][O:9][C:8]2[CH:15]=[CH:16][C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:17])[C:7]=2[O:12]1

Komponenten

4

Edukt 2

HCID 17749100Barium hydroxide, monohydrateHCID 687788313-Hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid methyl ester

Produkt 1

HCID 687762923-Hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a round bottom flask equipped with magnetic stirring was added 3-hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid methyl ester (6.40 g, 26.9 mmol), barium hydroxide monohydrate (25.44 g, 134.3 mmol), and methanol (108 mL). This mixture was stirred at room temperature for 24 hours. The methanol was evaporated. The resulting slurry was taken up in water and washed once with ether. The aqueous layer was acidified by pouring into iced concentrated HCl. This was extracted twice with ethyl acetate. The ethyl acetate extracts were combined, dried over magnesium sulfate, filtered and evaporated to give a yellow solid, 3-hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid, (4.82 g, 21.5 mmol) in 80% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 2.45 (s, 3H), 3.85 (m, 2H), 4.12 (m, 1H), 4.24 (m, 1H), 4.41 (m, 1H), 6.76 (d, 1H), 7.51 (d, 1H); TLC: Rf=0.32 (1:1 ethyl acetate/hexane).

Aufarbeitung

  1. customTo a round bottom flask equipped
  2. stirringThis mixture was stirred at room temperature for 24 hours
  3. customThe methanol was evaporated
  4. washwashed once with ether
  5. additionby pouring into iced concentrated HCl
  6. extractionThis was extracted twice with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a6d0e7e8ec23429781fd2937a8245006
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748125B2

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