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

HRID 353026Notes

Reaction equation

HRID 353026 reaction equation
[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

Participants

4

Reactant 3

HCID 1057PyrogallolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79a468d4dcfe4bc3946797cfba5a520c
Source dataset
uspto-grants-2004_06
Patent number
US06750049B1

Reaction notes

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