Phenol → HCID 21957453, compound

HRID 2213575Notes

Reaction equation

HRID 2213575 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CS([O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:16]=[O:17])(=O)=O.[C:30]1(O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[O:11]([CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:16]=[O:17])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 21957488HCID 21957488, compound

Product 1

HCID 21957453HCID 21957453, compound

Procedure

Cesium carbonate (226 mg, 0.69 mmol, 1.5 eq) was added to a stirred solution of 3-[[(methylsulfonyl)oxy]methyl]-4-(2-phenylethoxy)benzaldehyde (155 mg, 0.46 mmol, 1 eq) and phenol (175 mg, 1.86 mmol, 4 eq). The reaction mixture was stirred for 48 h, then partitioned between diethyl ether (50 mL) and water (50 mL). The two layers were separated and the organic layer washed with water (2×100 mL), 1M sodium hydroxide (100 mL), brine (100 mL) and then dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel. Elution with dichloromethane gave a gummy solid, which when triturated with ether crystallized to a white powder (105 mg, 68%). RF (petroleum ether:diethyl ether, 1:1) 0.40. 1H NMR (CDCl3) δ 9.90 (s, 1H, O═C—H), 8.04 (s, 1H, ArH), 7.84 (d, 1H, J 8.4 Hz, ArH), 5.08 (s, 2H, CH2OPh), 4.34 (t, 2H, J 6.5 Hz, OCH2CH2Ph), 3.16 (t, 2H, J 6.5 Hz, OCH2CH2Ph).

Workup

  1. custompartitioned between diethyl ether (50 mL) and water (50 mL)
  2. customThe two layers were separated
  3. washthe organic layer washed with water (2×100 mL), 1M sodium hydroxide (100 mL), brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washElution with dichloromethane
  8. customgave a gummy solid, which when
  9. customtriturated with ether
  10. customcrystallized to a white powder (105 mg, 68%)

Sources & evidence

ORD record
ord-8b2f9395c40b4090863c9823bb0a15fd
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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