Acetone → HCID 131730913, compound

HRID 1045120Notes

Reaction equation

HRID 1045120 reaction equation
[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3].[CH3:7][O:8][C:9]([CH3:11])=[CH2:10].OP(O)(O)=O.CC(C)=O.C(N(CC)CC)C>>[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3].[CH3:7][O:8][C:9]([CH3:11])=[CH2:10]

Participants

6

Reactant 5

HCID 180AcetoneHCID 1004Phosphoric AcidHCID 82572-Methyl-3-buten-2-olHCID 83002-MethoxypropeneHCID 8471Triethylamine

Product 1

HCID 131730913HCID 131730913, compoundYield 87.2%

Procedure

A mixture of 52.2 g (0.592 mol) of 2-methyl-3-buten-2-ol (MBE) and of 331.9 g (4.44 mol) of isopropenyl methyl ether (IPM) was stirred by a magnetic stirrer in a 1 L 3-neck round bottomed flask under argon at a temperature of −30° C. 3.72 g of a catalyst solution consisting of 17.7 weight-% H3PO4 in acetone (=1 mol-% relative to MBE) were added at once with the help of a volume adjustable pipette with disposable tip. The clear and colourless solution was stored for 72 hours at a temperature of −26° C. in a deep freezer. Under stirring and argon the solution was set basic by addition of 1.81 g (2.485 ml, 0.018 mol) of triethylamine and allowed to reach room temperature (22° C.). The reaction mixture was then concentrated on a rota-vapor under a pressure of 75 mbar at a temperature not exceeding 22-25° C. 94.9 g of crude 3-(1-methoxy-1-methyl-ethoxy)-3-methyl-but-1-ene, including 2.4 g of triethylammonium phosphate, were obtained containing 88.4 g of MMMB or MBE-IPM-adduct (yield: 87.2% relative to MBE).

Workup

  1. additionwere added at once with the help of a volume adjustable pipette with disposable tip
  2. customto reach room temperature
  3. custom(22° C.)
  4. concentrationThe reaction mixture was then concentrated on a rota-vapor under a pressure of 75 mbar at a temperature not
  5. customexceeding 22-25° C
  6. customwere obtained

Sources & evidence

ORD record
ord-c59c0a80c07c42a2a5f44994b4a6bf60
Source dataset
uspto-grants-2013_10
Patent number
US08563780B2

Reaction notes

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