Hydrochloric Acid → 2-Benzylacrylic Acid

HRID 9782

반응식

HRID 9782 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8021DiethylamineHCID 12031Benzylmalonic acid

생성물 1

HCID 3035712-Benzylacrylic Acid수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-bbd607b812354346904cf9218fbabf16
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091354B2

연결된 노트

불러오는 중…