Sodium Hydroxide → Benzenepropanoic acid

HRID 1015576

반응식

HRID 1015576 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 107Benzenepropanoic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-861d3dce1b7d47cda12181c894b36cf1
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985772B2

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