Ethanol → HCID 13125676, compound

HRID 1706775Notes

Reaction equation

HRID 1706775 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH2:13][C:12]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[O:14]2)[O:11][N:10]=1.OS(O)(=O)=O.[CH2:28](O)[CH3:29]>CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]([O:14][CH2:28][CH3:29])=[O:22])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13071261HCID 13071261, compound

Product 1

HCID 13125676HCID 13125676, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 4 g. (0.011 mole) of 3'-(2,4-dichlorophenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one, 2 ml. of concentrated H2SO4 and 200 ml. of ethanol was held at reflux for 19 hours, cooled, and poured into ice water. The resultant mixture was extracted twice with ether. The ethereal solution was washed twice with water, dried over CaSO4 and concentrated under vacuum to give an oil. The oil was dissolved in hot hexane to afford 4.2 g. of a crystalline solid (96.9%). Recrystallization of the solid from hexane gave 3.1 g. of pure product; m.p. 85°-86° C.

Workup

  1. temperatureat reflux for 19 hours
  2. temperaturecooled
  3. extractionThe resultant mixture was extracted twice with ether
  4. washThe ethereal solution was washed twice with water
  5. dry with materialdried over CaSO4
  6. concentrationconcentrated under vacuum
  7. customto give an oil
  8. customto afford 4.2 g
  9. customRecrystallization of the solid from hexane
  10. customgave 3.1 g

Sources & evidence

ORD record
ord-b5361c9b4d8c49efbc53715b5948b6e7
Source dataset
uspto-grants-1980_06
Patent number
US04208510

Reaction notes

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