Bromoacetic Acid → 2-Naphthoxyacetic acid

HRID 714236

반응식

HRID 714236 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].Br[CH2:13][C:14]([OH:16])=[O:15]>CC(CC)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:13][C:14]([OH:16])=[O:15]

참가 물질

4

반응물 2

HCID 6227Bromoacetic AcidHCID 86632-Naphthol

생성물 1

HCID 84222-Naphthoxyacetic acid수율 75.2%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매2회

반응 조건

온도
50 °C

실험 절차

In a two-neck flask provided with a condenser and placed under an inert atmosphere, 2-naphthol (3.0 g, 20 mmol) is dissolved in 95 mL of methylethylketone (MEK) in the presence of soda (40 g, 93 mmol), and then heated to 50° C. for 30 minutes. 2-bromoethanoic acid (5.76 g, 41 mmol) dissolved in 23 mL of MEK is added dropwise under hot conditions. The heating is maintained for a further 4 hours. The reaction medium is cooled to room temperature and then filtered. The solid collected by filtration is taken up in a mixture of ethyl acetate and of 1N HCl in water. Both phases are separated and the aqueous phase is extracted once with ethyl acetate. The organic phases are collected, dried on magnesium sulfate, filtered and concentrated until the first crystals appear. Heptane is added (about 20% of the remaining volume), and the formed precipitate is recovered, rinsed with heptane and dried until it has constant weight in order to obtain 3.04 g (72%) of (naphthalen-2-yloxy)acetic acid as a white solid.

후처리

  1. customIn a two-neck flask provided with a condenser
  2. additionis added dropwise under hot conditions
  3. temperatureThe heating is maintained for a further 4 hours
  4. temperatureThe reaction medium is cooled to room temperature
  5. filtrationfiltered
  6. filtrationThe solid collected by filtration
  7. additionis taken up in a mixture of ethyl acetate and of 1N HCl in water
  8. customBoth phases are separated
  9. extractionthe aqueous phase is extracted once with ethyl acetate
  10. customThe organic phases are collected
  11. customdried on magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated until the first crystals
  14. additionHeptane is added (about 20% of the remaining volume), and the formed precipitate
  15. customis recovered
  16. washrinsed with heptane
  17. customdried until it

출처 및 근거

ORD 기록
ord-7b5e2819701a45229d1f3b5320b2d7d3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187438B2

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