Hydroquinone → 4-But-2-ynyloxy-phenol

HRID 12932Notes

Reaction equation

HRID 12932 reaction equation
[C:1](Br)#[C:2][CH2:3][CH3:4].[C:6]1([CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)[OH:7].C([O-])([O-])=O.[K+].[K+]>>[CH2:1]([O:7][C:6]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 109970821-Bromobut-1-yne

Product 1

HCID 226340454-But-2-ynyloxy-phenolYield 25%

Procedure

To a solution containing butynyl bromide (1 g, 7.5 mmol), hydroquinone (827 mg, 7.5 mmol), and K2CO3 (1.04 g, 7.5 mmol) was refluxed for 10 h. Solvent was removed in vacuo and the crude product was dissolved in EtOAc and partitioned with water. Organic layer was separated and washed with water and dried over anhydrous Na2SO4. The solvent was removed in vacuo to obtain the crude product (0.3 g, 25%), which was used for the next step without further purification; LCMS 99%, m/z 162.2 (M+).

Workup

  1. temperaturewas refluxed for 10 h
  2. customSolvent was removed in vacuo
  3. dissolutionthe crude product was dissolved in EtOAc
  4. custompartitioned with water
  5. customOrganic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3460ff4893ad4905a99f8400ac94a8e1
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Reaction notes

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