Hydrochloric Acid → 7-(Benzyloxy)-2-naphthoic acid

HRID 890955노트

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HRID 890955 반응식
[OH-:1].[K+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([C:21]#N)=[CH:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC=CC=1.Cl.[OH2:31]>C(O)C>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17]([C:21]([OH:31])=[O:1])=[CH:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 222434287-(Benzyloxy)naphthalene-2-carbonitrile

생성물 1

HCID 222434307-(Benzyloxy)-2-naphthoic acid수율 72%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

KOH (406 mg, 7.3 mmol) is added to a suspension of 7-benzyloxy-2-naphthonitrile (626 mg; 2.42 mmol) in water, ethanol, and toluene (15 mL, 1:3:2). The reaction is heated to 80° C. for 72 hours. The reaction is allowed to cool, poured into 1M HCl and extracted three times with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The product is purified by column chromatography (step gradient, 5 to 10% methanol in CH2Cl2). The resulting material is crystallized from ethanol-water to give 7-benzyloxy-2-naphthoic acid (484 mg, 72%) as a white solid. HRMS (EI) calculated for C18H14O3: 278.0943, found 278.0947.

후처리

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe product is purified by column chromatography (step gradient, 5 to 10% methanol in CH2Cl2)
  7. customThe resulting material is crystallized from ethanol-water

출처 및 근거

ORD 기록
ord-371734b6b9ca4c608cec735d8d423c8b
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001900B2

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