Sulfuric Acid → (alphaR)-Acetyloxybenzenebutanoic Acid

HRID 845249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845249
[OH:1][C@H:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22].S(=O)(=O)(O)O>ClCCl.CN(C)C1C=CN=CC=1>[C:21]([O:1][C@H:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4])(=[O:23])[CH3:22]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 2759328(R)-2-Hydroxy-4-phenylbutyric acid

Produkt 1

HCID 14772849(alphaR)-Acetyloxybenzenebutanoic AcidAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A(ii)(a) A solution of 18 g of 2(R)-hydroxy-4-phenylbutanoic acid in 200 ml of dichloromethane containing 20.5 g of triethylamine and 250 mg of 4-(dimethylamino)pyridine was stirred at room temperature and treated dropwise with 12 g of acetic anhydride. The resulting mixture was stirred for a further 3 hours and then acidified by the addition of 125 ml of 2N sulphuric acid. The organic phase was separated and washed with two 100 ml portions of 2N sulphuric acid, then with 100 ml of water and finally with 100 ml of saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated in vacuo to give 22 g of 2(R)-acetoxy-4-phenylbutanoic acid as a colouless viscous oil; [α]43620 =+13.7° (c=1 in ethanol).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with two 100 ml portions of 2N sulphuric acid
  3. dry with materialwith 100 ml of water and finally with 100 ml of saturated sodium chloride solution, dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97ddb0535bd546fdb2011e8c2be99a4d
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04757069

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