2-Chloronaphthalene → 2-(2-Naphthyl)-6-hydroxybenzoxazole

HRID 1591040

반응식

HRID 1591040 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1Cl.Cl.[NH2:13][C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1[OH:21].[OH-].[Na+].[CH2:24]1COCC1>CO.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[C:24]1[O:21][C:15]2[CH:16]=[C:17]([OH:18])[CH:19]=[CH:20][C:14]=2[N:13]=1

참가 물질

7

반응물 4

HCID 70562-ChloronaphthaleneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 134088224-Aminobenzene-1,3-diol hydrochloride

생성물 1

HCID 197660272-(2-Naphthyl)-6-hydroxybenzoxazole수율 47.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

20 g (104.9 mmol) of 2-naphthyl chloride and 2.5 g (15.5 mmol) of 4-aminoresorcinol hydrochloride were introduced into a three-necked flask provided with a thermometer and a cooling condenser, and the mixture was heated at 135° to 205° C. for 1 hour, then excessive acid chloride was removed by distillation. To the residue, 8.3 g (207.5 mmol) of NaOH, 60 ml of THF, 60 ml of water and 30 ml of methanol were added, and the mixture was stirred at room temperature for about 2 hours. The reaction solution was extracted with ethyl acetate, the extract was washed with saturated sodium chloride water solution, and ethyl acetate was distilled off. Recrystallizing the residue with water/methanol/THF and drying the crystal, there was obtained 1.92 mg (7.36 mmol) of 2-(2-naphthyl)-6-hydroxybenzoxazole. The yield was 47.5%.

후처리

  1. customprovided with a thermometer and a cooling condenser
  2. temperaturethe mixture was heated at 135° to 205° C. for 1 hour
  3. customexcessive acid chloride was removed by distillation
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washthe extract was washed with saturated sodium chloride water solution, and ethyl acetate
  6. distillationwas distilled off
  7. customRecrystallizing the residue with water/methanol/THF
  8. customdrying the crystal

출처 및 근거

ORD 기록
ord-7d59f3617b824bcdb9d430a7dd9c0ccb
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206149

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