Pyrogallol → 1,1',1''-[Benzene-1,2,3-triyltris(oxymethylene)]tribenzene

HRID 353026ノート

反応式

HRID 353026 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[K+].[K+].[C:15]1([CH:23]=[CH:22][CH:21]=[C:19]([OH:20])[C:17]=1O)[OH:16]>>[CH2:1]([O:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:15]([O:16][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]=1[O:12][CH2:9][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 1057PyrogallolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 205433631,1',1''-[Benzene-1,2,3-triyltris(oxymethylene)]tribenzene収率 83%

実験手順

Lowe, W. et al., Arch. Pharm. (Weinheim) 327:255 (1994). Benzyl bromide (57 mL, 0.481 mol) and then K2CO3 (100 g, 0.725 mol) were added to a solution of pyrogallol (20 g, 0.1 59 mol) in 200 mL dry, degassed acetone under Ar. This reaction mixture was subsequently stirred for 30 min at room temperature and then for 24 h at reflux under Ar. A solution of NaOH (1.6 g) in MeOH (32 mL) was then added and the reaction refluxed for an additional 30 min. After cooling to room temperature, solids were filtered and washed with acetone. The filtrate was concentrated and the residue recrystallized from MeOH to afford 8 (52 g, 83%) as an off-white solid. mp 67-68° C. 1H NMR (CDCl3): δ7.44-7.19 (m, 15 H), 6.85 (dd, J=9, 9 Hz, 1 H), 6.57 (d, J=8.2 Hz, 2 H), 5.05 (s, 2 H), 5.02 (s, 4 H). 13C NMR (CDCl3): δ152.9, 138.4, 137.8, 137.0, 128.4, 128.3, 128.0, 127.8, 127.6 (2), 127.3, 127.2, 123.5, 107.7, 75.0, 70.9.

後処理

  1. customdry
  2. customdegassed acetone under Ar
  3. temperaturefor 24 h at reflux under Ar
  4. additionA solution of NaOH (1.6 g) in MeOH (32 mL) was then added
  5. temperaturethe reaction refluxed for an additional 30 min
  6. temperatureAfter cooling to room temperature
  7. filtrationsolids were filtered
  8. washwashed with acetone
  9. concentrationThe filtrate was concentrated
  10. customthe residue recrystallized from MeOH

出典と根拠

ORDレコード
ord-79a468d4dcfe4bc3946797cfba5a520c
出典データセット
uspto-grants-2004_06
特許番号
US06750049B1

反応ノート

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