Water → HCID 22107073, compound

HRID 1456544Notes

Reaction equation

HRID 1456544 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([I:11])[CH:5]=1)=[O:3].[OH-].[Na+].O.Cl[C:16]([CH3:20])([CH3:19])[C:17]#[CH:18]>C1(C)C(C)=CC=CC=1>[C:2]([C:4]1[CH:5]=[C:6]([I:11])[C:7]2[O:10][C:16]([CH3:20])([CH3:19])[CH:17]=[CH:18][C:8]=2[CH:9]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 10515151-(4-hydroxy-3-iodophenyl)ethanone

Product 1

HCID 22107073HCID 22107073, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-hydroxy-3-iodoacetophenone (5.24 g), 40% sodium hydroxide solution (4.8 ml), water (19 ml), xylene (11 ml) and 3-chloro-3-methylbut-1-yne (4.1 g) was heated to 90° C. for 3 hrs. The mixture was cooled and extracted with ether, and the ether extracts were washed with 2N sodium hydroxide solution, water and brine and dried over anhydrous sodium sulphate. The ethereal solution was filtered and evaporated, and the xylene solution that remained was refluxed for 16 hrs. The solution was evaporated and the residue chromatographed on silica gel using 10% ethyl acetate in hexane to give 6-acetyl-8-iodo-2,2-dimethyl-2H-1-benzopyran as a colourless solid (3.07 g), m.p. 102° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether
  3. washthe ether extracts were washed with 2N sodium hydroxide solution, water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationThe ethereal solution was filtered
  6. customevaporated
  7. temperaturethe xylene solution that remained was refluxed for 16 hrs
  8. customThe solution was evaporated
  9. customthe residue chromatographed on silica gel using 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9b3c8f8b5c4d444f92184df556431a8b
Source dataset
uspto-grants-1998_12
Patent number
US05843989

Reaction notes

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