Sodium Hydroxide → Benzenepropanoic acid

HRID 131766

反応式

HRID 131766 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 107Benzenepropanoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-e496ded3a55c4c318574df62fccb62fc
出典データセット
uspto-grants-2008_06
特許番号
US07384980B2

関連ノート

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