Water → 1-Heptyn-1-ylbenzene

HRID 269426Notes

Reaction equation

HRID 269426 reaction equation
[Cr](O)(O)(=O)=O.[C:6]1([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>CC(C)=O>[C:6]1([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24425Chromic Acid2×HCID 589246797-Phenylhept-6-yn-1-ol

Product 1

HCID 843971-Heptyn-1-ylbenzeneYield 105.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Brown's chromic acid reagent (133 mL, 88 mmol, 0.66 M) was added slowly in drops to a magnetically stirred solution of 7-phenylhept-6-yn-1-ol (6) (7.53 g, 40 mmol) in acetone (400 mL) at 0° C. After the chromic acid had been added, the reaction mixture was stirred for 1 hour at 0° C. and then at room temperature until all the base material has been converted as indicated by TLC. Water (300 mL) was added and the aqueous phase was then extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (6×50 mL). The combined organic phases were washed with water (2×25 mL) and dried (MgSO4). Distillation on a rotary evaporator yielded 7.3 g (90%) of a pale yellow viscous oil, which crystallized when left to rest. TLC and NMR indicated a pure product.

Workup

  1. customat room temperature
  2. extractionthe aqueous phase was then extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (6×50 mL)
  3. washThe combined organic phases were washed with water (2×25 mL)
  4. dry with materialdried (MgSO4)
  5. distillationDistillation
  6. customon a rotary evaporator

Sources & evidence

ORD record
ord-6c0b4013cad442dc9154817e6ab90bef
Source dataset
uspto-grants-2008_11
Patent number
US07446226B2

Reaction notes

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