Water → HCID 22153855, compound

HRID 1110652Notes

Reaction equation

HRID 1110652 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.[CH2:20]([O:24][CH2:25][CH2:26]O)[CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.[OH2:35]>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][CH2:26][CH2:25][O:24][CH2:20][CH2:21][CH2:22][CH3:23])=[O:35])[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81332-ButoxyethanolHCID 8471TriethylamineHCID 22153851HCID 22153851, compound

Product 1

HCID 22153855HCID 22153855, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Crude 12H-dibenzo[d,g][1,3]dioxocin-6-carbonyl chloride (4.8 g, 17.5 mmol) is dissolved in toluene and treated with a solution of 2-butoxyethanol (2.77 ml, 21 mmol) and 5 ml of triethylamine in toluene at 0° C. under argon. The mixture is heated at reflux for 2 hours and then cooled to room temperature The mixture is poured into 150 ml of water and extracted with 4×100 ml of ethyl acetate. The organic solution is washed with 5 percent hydrochloric acid, 5 percent sodium hydroxide and then brine, dried with magnesium sulfate and filtered. The solvent is removed to leave a yellow liquid which is chromatographed on dry column silica gel, using ethyl ether/hexane (1:2) as the solvent, to give a yellowish oil (4.3 g, 69 percent) An analytically pure material is obtained by using prep thin layer chromatography. IR (neat) 1770, 1582 cm-1. 1H NMR (CDCl3) δ 0.75-1.3 (m, 3H, CH3), 1.2-2.0 (m, 4H, CH2), 3.3-4.0 (m, 5H, OCH2 and benzylic), 4.4-4.9 (m, 3H, OCOCH2 and benzylic), 5.6 (s, 1H, CH), 6.9-7.5 (m, 8H, aromatic).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with 4×100 ml of ethyl acetate
  4. washThe organic solution is washed with 5 percent hydrochloric acid, 5 percent sodium hydroxide
  5. dry with materialbrine, dried with magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed
  8. customto leave a yellow liquid which
  9. customis chromatographed
  10. customon dry column silica gel

Sources & evidence

ORD record
ord-aac4c9bc9ee64ce6b56ba74a17972b6c
Source dataset
uspto-grants-1990_12
Patent number
US04976770

Reaction notes

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