Phosphoric Acid → 5-Cyclopentylidenepentan-2-one

HRID 1471381Notes

Reaction equation

HRID 1471381 reaction equation
[CH:1]([C:3]1(O)[CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].C[O:10][C:11]([CH3:13])=[CH2:12].P(=O)(O)(O)O.C(N(CC)CC)C>CC(OC)(C)C>[C:3]1(=[CH:1][CH2:2][CH2:12][C:11](=[O:10])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 83002-MethoxypropeneHCID 8471TriethylamineHCID 317028Vinylcyclopentanol

Product 1

HCID 135280135-Cyclopentylidenepentan-2-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
130 °C

Procedure

In an autoclave under N2, a mixture of 1-vinylcyclopentanol (65 g, 0.58 mol), 2-methoxypropene (108 ml, 1.15 mol), 85% phosphoric acid (0.29 ml), triethylamine (0.63 ml) was heated at 130° C. for 15 h. The reaction mixture was cooled to 20° C., diluted with MTBE (500 ml), washed three times with water (25 ml), once with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4) and concentrated. Widmer-Distillation (0.13 mbar, head temp. 58° C.) of the crude product gave 5-cyclopentylidenepentan-2-one (63.67 g, 72%).

Workup

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. washwashed three times with water (25 ml)
  3. dry with materialonce with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4)
  4. concentrationconcentrated
  5. distillationWidmer-Distillation (0.13 mbar, head temp. 58° C.) of the crude product

Sources & evidence

ORD record
ord-93c49396527747c4b038abd950325bd9
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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