Methanol → Methyl 3-hydroxy-3,7-dimethyl-6-octenoate

HRID 1934852Notes

Reaction equation

HRID 1934852 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[O:5][C:4](=[O:6])[CH2:3]1.S([O-])(O)(=O)=O.[Na+].[CH3:19][OH:20]>>[CH3:19][O:20][C:4](=[O:6])[CH2:3][C:2]([CH3:1])([OH:5])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 516919Sodium BisulfateHCID 11263723HCID 11263723, compound

Product 1

HCID 20744966Methyl 3-hydroxy-3,7-dimethyl-6-octenoateYield 88.6%

Conditions

Temperature
10 °C

Procedure

0.69 g of Na metal were dissolved in 200 g of methanol and cooled to 10° C. 50.47 g (0.279 mol) of 4-methyl-4-(4-methylpent-3-en-1-yl)-2-oxetanone were then added over a period of 17 mins, during which time the temperature rose to 16° C. Next, the mixture was stirred at 20° C. for 1.2 h and then acidified with 4.14 g (30 mmol) of sodium hydrogen sulfate. After being stirred for a further 1.7 h at 20° C., the suspension was filtered. The filtrate was concentrated (80 mbar, 40° C.). The residue (56.56 g) was then fractionated at 1 mbar, and the main fraction distilled at 95° C. to 97° C. 49.52 g (87.1%) of the title product were obtained in the form of an oil.

Workup

  1. customrose to 16° C
  2. stirringAfter being stirred for a further 1.7 h at 20° C.
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated (80 mbar, 40° C.)
  5. distillationthe main fraction distilled at 95° C. to 97° C

Sources & evidence

ORD record
ord-9625f1a7fc3e44299ed805ea4d8047df
Source dataset
uspto-grants-2002_05
Patent number
US06384242B1

Reaction notes

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