Hydrochloric Acid → 7-Chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol

HRID 238610노트

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HRID 238610 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](O)=[O:19])[C:12]([CH3:21])=[C:11]2[OH:22].Cl>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15]([CH:14]=[C:13]([CH2:18][OH:19])[C:12]([CH3:21])=[C:11]2[OH:22])=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 593265616-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid

생성물 1

HCID 593264967-Chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

To a slurry of lithium aluminum hydride (4.1 g) in tetrahydrofuran (80 mL) was added a solution of 6-chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid (12.7 g, 54 mmol) in tetrahydrofuran (80 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 5 hours, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The aqueous layer was extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine (200 mL×2), dried over sodium sulfate and concentrated in vacuo to give 7-chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol (8.5 g, 71%) as a white solid.

후처리

  1. temperaturethe resulting mixture was cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×4)
  5. washThe combined organic layers were washed with brine (200 mL×2)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2af500168d964a649f5edc4af6ab1a98
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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