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

HRID 487887

反応式

HRID 487887 の反応式
[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

参加物

4

反応物 2

HCID 950732,3-Naphthalenedicarboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5984172,3-Bis(hydroxymethyl)naphthalene収率 84.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2,3-naphthalenedicarboxylic acid (4.6 g, 0.023 mole) in dry THF (135 mL, wanned to 50° C. to maintain solution) is added dropwise over 15 minutes to a 1.15 M 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.).

後処理

  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

出典と根拠

ORDレコード
ord-f9c5095c8d144c6aa478d87d79b9ddf2
出典データセット
uspto-grants-1994_03
特許番号
US05298498

関連ノート

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