Einecs 211-027-4 → 4-[5-Methoxy-2-(phenylethynyl)phenyl]butan-2-one

HRID 623162Notes

Reaction equation

HRID 623162 reaction equation
O[C:2]1([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]([CH2:8][CH2:9][C:10]2([CH3:18])OCC(C)(C)C[O:11]2)[CH2:6][C:5](=[O:19])[CH:4]=[CH:3]1.[Cl-].[NH+]1C=CC=C[CH:30]=1>CO>[CH3:30][O:19][C:5]1[CH:4]=[CH:3][C:2]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:7]([CH2:8][CH2:9][C:10](=[O:11])[CH3:18])[CH:6]=1

Participants

4

Reactant 2

HCID 69401Einecs 211-027-4HCID 212923464-Hydroxy-4-(phenylethynyl)-5-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-cyclohexen-1-one2×

Product 1

HCID 140254764-[5-Methoxy-2-(phenylethynyl)phenyl]butan-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-4-(phenylethynyl)-5-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]-2-cyclohexene-1-one (4 g, 0.011 mole), the title product of Example 1c, pyridinium chloride (2.5 g, 0.022 mole) and absolute methanol (30 mL) were combined and heated to reflux for 4 hr. The reaction mixture was quenched into 50 mL of water, ether was added, the resulting layers separated, the aqueous layer extracted with ether, the ether extracts combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 3.0 g of the title product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hr
  3. customThe reaction mixture was quenched into 50 mL of water, ether
  4. additionwas added
  5. customthe resulting layers separated
  6. extractionthe aqueous layer extracted with ether
  7. washwashed with water, brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b235f643d7864203a445868786087ed2
Source dataset
uspto-grants-1988_09
Patent number
US04772755

Reaction notes

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