Hydrochloric Acid → HCID 66974036, compound

HRID 1948752Notes

Reaction equation

HRID 1948752 reaction equation
Cl.[CH3:2][C:3]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH:6]([CH3:11])[C:5](=[O:12])[CH2:4]2.[CH3:13]OC(OC)OC.[CH2:20](O)[CH:21]=C>CS(O)(=O)=O.C(O)(=O)C.CO>[CH2:11]([C:6]1([CH3:13])[CH:7]2[CH2:10][C:3]([CH3:2])([CH2:9][CH2:8]2)[CH2:4][C:5]1=[O:12])[CH:20]=[CH2:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7858Allyl AlcoholHCID 9005Trimethyl orthoformateHCID 66974043HCID 66974043, compound

Product 1

HCID 66974036HCID 66974036, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Hydrochloric acid (HCl, 6 g) was added to a solution of 1,4-dimethyl-bicyclo[3.2.1]octan-3-one (400 g, 2.6 mol, obtained as above in EXAMPLE III), trimethylorthoformate (HC(OCH3)3, 280 g, 2.6 mol), and methanol (CH3OH, 400 mL). The reaction mixture was aged for 3 hours and subsequently quenched with a NaOH solution. Allyl alcohol (CH2CHCH2OH, 300 g, 5.2 mol), acetic acid (CH3COOH, 50 g), and methanesulfonic acid (CH3SO2OH, MSA, 5 g) were added and aged at reflux. The volatile ingredients were distilled off with a Dean Stark trap. The resulting mixture was washed with a Na2CO3 solution. Fractional distillation of the organic layer provided 4-allyl-1,4-dimethyl-bicyclo[3.2.1]octan-3-one (127 g) having a boiling point of 64° C. at a pressure of 0.2 mmHg.

Workup

  1. customsubsequently quenched with a NaOH solution
  2. temperatureat reflux
  3. distillationThe volatile ingredients were distilled off with a Dean Stark trap
  4. washThe resulting mixture was washed with a Na2CO3 solution
  5. distillationFractional distillation of the organic layer

Sources & evidence

ORD record
ord-1cbfe91d2958494dbe8f8c3c9d072c09
Source dataset
uspto-grants-2013_03
Patent number
US08399522B2

Reaction notes

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