Sodium Hydroxide → Benzenepropanoic acid

HRID 50590

Reaktionsgleichung

Reaktionsgleichung von HRID 50590
C[O:2][C:3](=[O:27])[CH2:4][CH:5](C1C=C(Br)C=CC=1OCC1C=CC=CC=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[C:6]1([CH2:5][CH2:4][C:3]([OH:27])=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21476697Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate

Produkt 1

HCID 107Benzenepropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (±)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionic acid methyl ester (0,391 g, 0,92 mmol) in ethanol (5 ml) was treated at 50° C. with excess aqueous sodium hydroxide solution until the milky emulsion became clear. The reaction mixture was then acidified (pH 3), evaporated and extracted with dichloromethane. The organic extract was evaporated and the remaining oil was redissolved in a minimum of boiling ethanol. The precipitation formed after 18 hrs at 4° C. was filtered off and dried in vacuo to yield 0.27 g (71.4%) of (±)-3-(2-Benzyloxy)-5-bromophenyl)-3-phenylpropionic acid, colourless crystals, m.p. 124.9° C.; tlc: (1) 0.15 starting material methyl ester 0.75); NMR (CDCl3): 39.15, 40.26, 70.25, 113.21, 113.90, 126.62, 127.27, 127.98, 128.17, 128.47, 128.54, 130.46, 130.68, 134.34, 136.45, 142.16, 154.95, 177.65. LC-MS: 412/410 (14/11%, M+), 394/392 (15/13%), 321/319 (17/22%), 304/302 (17/21%), 259 (24%), 194 (22%), 178 (21%), 167 (65%), 152 (49%), 92 (100%). IR (KBr): 3434, 3030, 1708, 1485, 1452, 1403, 1289, 1243, 1126, 1018, 804, 735, 698, 649. Calculated for C22H19BrO3 (mol-wgt. 411.30): C, 64.25%, H, 4.66%, Br, 19.43%, O, 11.67%; found: C, 63.72%, H, 4.70%, Br, 19.75%, O, 11.80%.

Aufarbeitung

  1. customevaporated
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. customwas evaporated
  5. dissolutionthe remaining oil was redissolved in a minimum of boiling ethanol
  6. customThe precipitation
  7. customformed after 18 hrs at 4° C.
  8. filtrationwas filtered off
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c12d9efec2774509b1d54bf7c0c5f74e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713464B1

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