Chloroacetic Acid → (3-Methylphenyl)-3-oxo-propanoic acid

HRID 1419091노트

반응식

HRID 1419091 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.ClC[C:12]([OH:14])=[O:13].[CH2:15]([OH:17])C.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]([CH:15]=[O:17])[C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 300Chloroacetic AcidHCID 702EthanolHCID 114763-Methylbenzyl alcoholHCID 24758Sodium hydride

생성물 1

HCID 22600148(3-Methylphenyl)-3-oxo-propanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 3-methylbenzyl alcohol (4.93 g, 40 mmol), chloroacetic acid (7.68 g, 81 mmol), and ethanol (0.04 mL) in 100 mL of anhydrous tetrahydrofuran was added to a mixture of sodium hydride (16.12 g, 403 mmol) in 50 mL anhydrous tetrahydrofuran dropwise over 55 minutes at 0° C. The cooling bath was removed and the solution was heated to reflux for 14.25 hours. The solution was cooled to room temperature, quenched with water and extracted with ether. The aqueous layer was acidified, extracted with ether, washed with brine, dried over MgSO4, and concentrated in vacuo to give (3-methylphenyl)-3-oxo-propanoic acid as an orange oil (6.58 g) which also contained chloroacetic acid. The oil was used in the next step without purification.

후처리

  1. customThe cooling bath was removed
  2. temperaturethe solution was heated
  3. temperatureto reflux for 14.25 hours
  4. customquenched with water
  5. extractionextracted with ether
  6. extractionextracted with ether
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b9a41050660a4482aba0de10e17c8a4f
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886016

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