Ethanol → HCID 46932893, compound

HRID 1295881Notes

Reaction equation

HRID 1295881 reaction equation
[C:1]([O-:4])([O-])=O.[Cs+].[Cs+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17](O)[C:18]2[C:19](=[O:31])[C:20]3[C:25]([O:26][C:27]=2[CH:28]=1)=[C:24]([O:29][CH3:30])[CH:23]=[CH:22][CH:21]=3)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI.CCO>CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([O:4][CH3:1])[C:18]2[C:19](=[O:31])[C:20]3[C:25]([O:26][C:27]=2[CH:28]=1)=[C:24]([O:29][CH3:30])[CH:23]=[CH:22][CH:21]=3)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 46935118HCID 46935118, compound

Product 1

HCID 46932893HCID 46932893, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (27.0 g, 83 mmol) was added in portions to phenol (102) (14.5 g, 42 mmol) and MeI (8.0 mL, 125 mmol) in DMF (400 mL) at rt. After 3 h at 50° C., the reaction was decanted and washed with CH2Cl2 into an erlenmeyer which had been placed in an ice cooled bath. With stirring, 2M HCl was added slowly until acidic by pH paper. After warming to rt, the reaction was diluted with CH2Cl2 (800 mL) and H2O (400 mL). The layers are separated and the aqueous layer was reextracted with CH2Cl2 (300 mL). The organic layers were combined, washed with brine (400 mL), dried (Na2SO4) and concentrated under reduced pressure to provide a red sludge which could be tritrated with EtOH and filtered to afford (9.3 g, 66%) of (103) as a pink solid. Analytically pure material can be obtained at this point by column chromatography with 50% EtOH/hexane. (LH-63-5) 1H NMR (250 MHz, CDCl3) δ 7.84 (d, 1H, J=6.0Hz), 7.42−7.31 (complex, 5H), 7.20−7.07 (complex, 2 H), 6.63 (s, 1H), 6.37 (s, 1H), 5.08 (s, 2H), 3.92 (s, 3H), 3.88 (s, 3H); 13C NMR (62.5 MHz) δ 175.2, 163.8, 161.7, 159.4, 147.8, 144.5, 135.6, 128.6, 128.3, 127.5, 123.9, 123.1, 117.5, 114.3, 106.1, 95.9, 93.6, 70.4, 56.3, 56.2; mass spectrum (CI) m/z+1 363.1242 [C22H19O5 (M+1) requires 363.1232] 363 (base), 339.

Workup

  1. customthe reaction was decanted
  2. washwashed with CH2Cl2 into an erlenmeyer which
  3. customhad been placed in an ice cooled bath
  4. addition2M HCl was added slowly until acidic
  5. additionthe reaction was diluted with CH2Cl2 (800 mL) and H2O (400 mL)
  6. customThe layers are separated
  7. washwashed with brine (400 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customto provide a red sludge which
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d73762b24bc6449394dee916396609c8
Source dataset
uspto-grants-2007_07
Patent number
US07244760B2

Reaction notes

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