Water → HCID 22153876, compound

HRID 1110656Notes

Reaction equation

HRID 1110656 reaction equation
[CH:1]1[C:12]2[CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[O:8][CH:7]([C:17](Cl)=[O:18])[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][CH2:22][CH2:23]O.C(N(CC)CC)C.[K+].[Br-].[OH2:34]>C1(C)C=CC=CC=1>[CH:1]1[C:12]2[CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[O:8][CH:7]([C:17]([O:18][CH2:23][CH2:22][O:21][CH3:20])=[O:34])[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 962WaterHCID 80192-MethoxyethanolHCID 8471TriethylamineHCID 253877Potassium BromideHCID 22153851HCID 22153851, compound

Product 1

HCID 22153876HCID 22153876, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

12H-Dibenzo[d,g][1,3]dioxocin-6-carbonyl chloride (5.33 g, 19.5 mmol) is dissolved in toluene and added to a solution of 2-methoxyethanol (2.2 ml, 27.6 mmol) and 7 ml of triethylamine in toluene at 0°-10° C. under argon. The mixture is heated at reflux for 3 hours, cooled to room temperature, poured into 150 ml of water and extracted with 4×100 ml of ethyl acetate The resultant organic solution is washed with 5 percent hydrochloric acid, 5 percent sodium hydroxide and brine, dried with magnesium sulfate and filtered. The solvent is removed to give a brownish solid which is chromatographed on dry column silica gel, using ethyl ether/hexane (1:1) as the solvent, to give a yellowish oil. This oil is solidified, the solid is filtered and washed with ethyl ether/hexane to yield a white solid: mp 74°-76° C. IR (KBr) 1779, 1581 cm-1 ; 1H NMR (CDCl3) δ 3.42 (s, 3H, CH3), 3.3-4.0 (m, 3H, CH and OCH2), 4.35-4.8 (m, 3H, CH and OCH2), 5.1 (s, 1H, OCHO), 6.9-7.45 (m, 8H, aromatic).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with 4×100 ml of ethyl acetate The resultant organic solution
  4. washis washed with 5 percent hydrochloric acid, 5 percent sodium hydroxide and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed
  8. customto give a brownish solid which
  9. customis chromatographed
  10. customon dry column silica gel
  11. customto give a yellowish oil
  12. filtrationthe solid is filtered
  13. washwashed with ethyl ether/hexane
  14. customto yield a white solid

Sources & evidence

ORD record
ord-f51b97b022564f508e09f96c70b29150
Source dataset
uspto-grants-1990_12
Patent number
US04976770

Reaction notes

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