Hydrochloric Acid → 2-Benzylacrylic Acid

HRID 1007586

反応式

HRID 1007586 の反応式
[CH2:1]([CH:8]([C:12](O)=O)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.C(NCC)C.Cl>C(OCC)(=O)C.O>[CH2:12]=[C:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8021DiethylamineHCID 12031Benzylmalonic acid

生成物 1

HCID 3035712-Benzylacrylic Acid収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of benzylmalonic acid (20.0 g, 0.103 mol, 1 eq) and paraformaldehyde (4.94 g, 0.164 mol, 1.6 eq) in ethyl acetate (150 mL) was cooled (0° C.) and treated with diethylamine (10.65 mL, 0.103 mol, 1 eq) drop wise, keeping the reaction temperature below 20° C. (see FIG. 6). The reaction was then warmed to reflux for 90 min and cooled again on ice. The homogeneous solution was treated with water (20 mL) and concentrated aqueous HCl (12N) (9.0 mL, 0.108 mol) drop wise, keeping the reaction temperature below 10° C. The phases were then separated. The organic layer was washed with brine (100 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under vacuum giving compound 17 as a white solid (15 g, 90%). Rf 0.46 (hexane/EtOAc=7:3). 1H NMR (300 MHz, CDCl3) δ 7.28 (m, 5H), 6.42 (s, 1H), 5.62 (s, 1H), 3.67 (s, 2H). [M−H]-161.0: tR=2.53 min; purity: 99%.

後処理

  1. customthe reaction temperature below 20° C. (see FIG. 6)
  2. temperatureThe reaction was then warmed
  3. temperatureto reflux for 90 min
  4. temperaturecooled again on ice
  5. customthe reaction temperature below 10° C
  6. customThe phases were then separated
  7. washThe organic layer was washed with brine (100 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under vacuum

出典と根拠

ORDレコード
ord-96c29b3acb0e4cc5bc1dcb50b531fd60
出典データセット
uspto-grants-2004_09
特許番号
US06794510B2

関連ノート

読み込み中…