Potassium Carbonate → HCID 22000662, compound

HRID 1976215Notes

Reaction equation

HRID 1976215 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1[OH:15].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:32][O:31][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:29][CH3:30])[CH2:22][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH2:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=2)[C:9]=1[OH:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 109004583,4-Dimethoxybenzyl bromideHCID 22000660HCID 22000660, compound

Product 1

HCID 22000662HCID 22000662, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-(3,5-Dimethoxybenzyloxy)-benzene-1,2-diol (0.28 g, 1.03 mmol), 4-bromomethyl-1,2-dimethoxy-benzene (0.24 g, 1.03 mmol), potassium carbonate (0.14 g, 1.03 mmol) and 18-crown-6-ether (0.03 g, 0.11 mmol) were stirred together at room temperature in acetone (30 cm3, 99%) under nitrogen for 21 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (10 cm3) and water (10 cm3). The aqueous layer was extracted with dichloromethane (2×10 cm3), and the combined extracts were washed with water (2×40 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was taken up in diethyl ether (30 cm3) and washed with sodium hydroxide (2×15 cm3, 3% aqueous solution). The sodium hydroxide portion was saturated with solid carbon dioxide pellets and extracted with diethyl ether (3×30 cm3). The extracts were evaporated under reduced pressure to give a crude oil. The oil was chromatographed (SiO2, heptane:ethyl acetate, 1:1) to give the phenol, (0.14 g, 31%) as a clear oil.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (2×10 cm3)
  3. washthe combined extracts were washed with water (2×40 cm3)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. washwashed with sodium hydroxide (2×15 cm3, 3% aqueous solution)
  7. extractionextracted with diethyl ether (3×30 cm3)
  8. customThe extracts were evaporated under reduced pressure
  9. customto give a crude oil
  10. customThe oil was chromatographed (SiO2, heptane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-4222506a54f148b28f21a85c7aff8eb6
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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