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

HRID 890955ノート

反応式

HRID 890955 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 222434307-(Benzyloxy)-2-naphthoic acid収率 72%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-371734b6b9ca4c608cec735d8d423c8b
出典データセット
uspto-grants-2006_02
特許番号
US07001900B2

反応ノート

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