Water → 4,4'-Oxybis(benzene-1,2-dimethanol)

HRID 1015458

反応式

HRID 1015458 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]3[C:20]([O:22][C:23](=O)[C:16]=3[CH:15]=2)=[O:21])=[CH:11][C:10]2[C:25]([O:27][C:28](=O)[C:9]=2[CH:8]=1)=[O:26].[OH-].[Na+].O>C1COCC1.CC(C)=O.CCOCC>[O:13]([C:14]1[CH:15]=[C:16]([CH2:23][OH:22])[C:17]([CH2:20][OH:21])=[CH:18][CH:19]=1)[C:12]1[CH:11]=[C:10]([CH2:25][OH:26])[C:9]([CH2:28][OH:27])=[CH:8][CH:7]=1

参加物

8

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 745744,4'-Oxydiphthalic anhydrideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 597794594,4'-Oxybis(benzene-1,2-dimethanol)収率 98.7%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of LiAlH4 (1M in THF) (64 mL, 64.0 mmol, 4.0 molar equivalents) in THF (50 mL) cooled to −78° C. is added dropwise a solution of 4,4′-oxydiphthalic anhydride (5.0 g, 9.6 mmol, 1 molar equivalent) in THF (20 ml). The reaction mixture is allowed to warm up to room temperature and then stirred at 70° C. for 2 hrs. To this resulting solution cooled at 0° C. is added a 2M sodium hydroxide solution (40 mL) followed by cold water (25 mL) and THF (50 mL). The reaction mixture is then further extracted with THF (3×50 mL). The organic fractions are combined, washed with brine, dried as added over magnesium sulfate, filtered and concentrated in vacuum to give a light brown oil. The crude oil is dissolved in acetone and Et2O is added until an off-white precipitate started to form. After filtration, the organic layer is concentrated in vacuum to give a light brown oil which crystallises spontaneously. Purification by DCM washes gave the title compound as a light yellow powder (2.75 g, 59%). 1H NMR (300.13 MHz, DMSO-d6) (ppm) 4.47 (d, J=5.40 Hz, 4H) 4.53 (d, J=5.40 Hz, 4H) 5.03 (t, J=5.40 Hz, 2H) 5.12 (t, J=5.40 Hz, 2H) 6.84 (dd, J1=2.70 Hz, J2=8.40 Hz, 2H) 7.04 (d, J=2.70 Hz, 2H) 7.34 (d, J=8.40 Hz, 2H).

後処理

  1. temperatureTo this resulting solution cooled at 0° C.
  2. extractionThe reaction mixture is then further extracted with THF (3×50 mL)
  3. washwashed with brine
  4. customdried
  5. additionas added over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give a light brown oil
  9. customto form
  10. filtrationAfter filtration
  11. concentrationthe organic layer is concentrated in vacuum
  12. customto give a light brown oil which
  13. customcrystallises spontaneously
  14. customPurification by DCM washes

出典と根拠

ORDレコード
ord-f9a05eaab0e94d1882bd54b12c0b85b6
出典データセット
uspto-grants-2011_07
特許番号
US07985353B2

関連ノート

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