2,3-Naphthalenedicarboxylic acid → 2,3-Bis(hydroxymethyl)naphthalene

HRID 2379026

반응식

HRID 2379026 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11](O)=[O:12])[C:2]=1[C:14](O)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:12][CH2:11][C:3]1[C:2]([CH2:14][OH:15])=[CH:1][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

참가 물질

4

반응물 2

HCID 950732,3-Naphthalenedicarboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 5984172,3-Bis(hydroxymethyl)naphthalene수율 84.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2,3-naphthalenedicarboxylic acid (4.6 g, 0.023 mole) in dry THF (135 mL, warmed to 50° C. to maintain solution) is added dropwise over 15 minutes to a 1.15M lithium aluminum hydride solution in THF (45 mL, 0.052 mole). The solution is stirred 3 hours after which TLC indicated consumption of diacid and formation of a new major product. The reaction is quenched carefully with THF-water, then 2N hydrochloric acid (40 mL) is added, and the resulting mixture is extracted 3 times with ether. The combined ether extracts are washed with water (2 times), with saturated sodium bicarbonate solution (1 time), with water, and are dried (sodium sulfate), filtered, and concentrated to give a tan solid (3.67 g). The solid is recrystallized from ethyl acetate giving the title compound (2.91 g) as a light tan crystalline material, mp 161°-162° C. (lit. ref mp 160° C.).

후처리

  1. customconsumption of diacid and formation of a new major product
  2. customThe reaction is quenched carefully with THF-water
  3. addition2N hydrochloric acid (40 mL) is added
  4. extractionthe resulting mixture is extracted 3 times with ether
  5. washThe combined ether extracts are washed with water (2 times), with saturated sodium bicarbonate solution (1 time), with water
  6. dry with materialare dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-30bd4f8a7d7044e483be8a0120685045
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05360797

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