Hydrochloric Acid → 5-Methoxynaphthalen-2-ol

HRID 890947

반응식

HRID 890947 반응식
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13]C)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[CH:10][C:9]([OH:13])=[CH:8]2

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 2969161,6-Dimethoxynaphthalene

생성물 1

HCID 149712425-Methoxynaphthalen-2-ol

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Bromocatecholborane (4.11 g, 20.7 mmol) is added to a solution of 1,6-dimethoxynaphthalene (3.89 g, 20.7 mmol) in dichloroethane (60 mL). The resulting solution is heated to reflux for 72 hours, allowed to cool, and then poured into 1N HCl. The resulting mixture is extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The product is purified by three columns (step gradient of 50–60–65%CH2Cl2 in hexanes) to give 5-methoxy-2-hydroxy naphthalene as an oil that solidifies on sitting (955 mg, 27%). 1H NMR (300 MHz, CDCl3) δ 8.17, 7.2–7.4, 7.0–7.1, 6.66, 5.08, 3.97.

후처리

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for 72 hours
  3. temperatureto cool
  4. extractionThe resulting mixture is extracted three times with CH2Cl2
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe product is purified by three columns (step gradient of 50–60–65%CH2Cl2 in hexanes)

출처 및 근거

ORD 기록
ord-c4bb5d7e19fc45d3bce496e97bd17320
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001900B2

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