Hydrochloric Acid → Hexanoic acid, 6-(phenylmethoxy)-

HRID 2194858ノート

反応式

HRID 2194858 の反応式
C1(=O)OCCCCC1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].Cl.[OH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].[OH-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:9]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 10401epsilon-CAPROLACTONEHCID 144906-Hydroxyhexanoic AcidHCID 14797Potassium HydroxideHCID 14798Sodium Hydroxide

生成物 1

HCID 10104963Hexanoic acid, 6-(phenylmethoxy)-収率 72%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

ε-caprolactone (10 mL, 0.18 mol), benzyl bromide (13.4 mL, 0.11 mol), and potassium hydroxide (11.3 g, 0.281 mol) were dissolved in toluene (200 mL). The reaction flask was placed in a 120° C. pre-heated oil bath and refluxed overnight under stirring. The mixture was then neutralized using 1 M HCl (300 mL), the toluene evaporated off, and the product extracted using dichloromethane (3×300 mL) to afford a mixture of mono and di-protected 6-hydroxy-hexanoic acid. The crude product was saponificated with 1M sodium hydroxide (200 mL) and methanol (200 mL), extracted with dichloromethane (3×200 mL), and the solvent was evaporated under reduced pressure to afford pure 6-benzyloxy-hexanoic acid (72% yield). 1H NMR (CDCl3) 1.38-1.46 (m, 2H, CH2), 1.57-1.68 (m, 4H, CH2CH2), 2.32-2.38 (m, 2H, CH2COOH), 3.42-3.46 (m, 2H, OCH2), 4.48-4.53 (s, 2H, PhCH2), 7.27-7.31 (m, 5H, aromatic).

後処理

  1. customwas placed in a 120° C.
  2. temperaturepre-heated oil bath
  3. temperaturerefluxed overnight
  4. customthe toluene evaporated off
  5. extractionthe product extracted
  6. customto afford
  7. extractionextracted with dichloromethane (3×200 mL)
  8. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-94951cfe114c4c32a42184da4a14896c
出典データセット
uspto-grants-2012_12
特許番号
US08334324B2

反応ノート

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