Sulfuric Acid → HCID 19375379, compound

HRID 1653938Notes

Reaction equation

HRID 1653938 reaction equation
C1O[C:4]2([C:7]([OH:15])([C:8]3[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=3)[C:6]([CH3:16])=[CH:5]2)[O:3]C1.OS(O)(=O)=O>C1COCC1.O.CCOCC>[OH:15][C:7]1([C:8]2[CH:9]=[CH:10][C:11]([I:14])=[CH:12][CH:13]=2)[C:4](=[O:3])[CH:5]=[C:6]1[CH3:16]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 19375380HCID 19375380, compound

Product 1

HCID 19375379HCID 19375379, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-hydroxy-4-p-iodophenyl-3-methyl-2-cyclobuten-1-one ethylene acetal (80 mg, 0.23 mmol dissolved in THF:H2O (3:1, 8 ml) was added dropwise 1N H2SO4 (3 ml) at room temperature. The reaction mixture was stirred for 4 h. The mixture was then diluted with ether (10 ml), and the organic fraction was separated from the aqueous phase by repeated extractions with ether (2×5 ml). The ether layer was dried over Na2SO4 and concentrated in vacuo to give a pale yellow oil (62 mg, 87%). 1H NMR (CDCl3) δ7.80 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 6.40 (s, 1H), 3.10 (s, 1H), 2.20 (s,3H).

Workup

  1. customthe organic fraction was separated from the aqueous phase
  2. extractionextractions with ether (2×5 ml)
  3. dry with materialThe ether layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fdde1885dd64684959009416d8fb5f5
Source dataset
uspto-grants-1995_04
Patent number
US05405598

Reaction notes

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