Hydrochloric Acid → 2-(3-Cyanophenoxy)acetic acid

HRID 1777097노트

반응식

HRID 1777097 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Br[CH2:11][C:12]([O:14]CC)=[O:13].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>CC#N.O.CCO>[C:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([OH:14])=[O:13])#[N:6]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 14798Sodium Hydroxide

생성물 1

HCID 122222682-(3-Cyanophenoxy)acetic acid

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 19096565Water ethanol용매

반응 조건

온도
80 °C

실험 절차

To a stirred mixture of 3-hydroxybenzonitrile (100 mg, 0.840 mmol) in MeCN (5 mL) was added ethyl bromoacetate (209 mg, 1.26 mmol) and K2CO3 (350 mg, 2.52 mmol). The mixture was stirred at 80° C. for 4 hours until TLC showed completion of the reaction. The mixture was filtered and the filtrate concentrated. NaOH (67 mg, 1.68 mmol) and water:EtOH (1:1, 10 mL) was added to the residue and the mixture stirred at 50° C. for 4 hours. After cooling, the mixture was acidified by 1M HCl, extracted with ethyl acetate (2×30 mL). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated. The residue was used directly in the next step. LCMS (m/z): 178.0 (M+1).

후처리

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. stirringthe mixture stirred at 50° C. for 4 hours
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate (2×30 mL)
  7. washThe combined extracts were washed with brine (30 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c51e6cde54ff4a5fafe78644fa973e99
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266836B2

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