Dimethyl Sulfate → HCID 54189322, compound

HRID 917981Notes

Reaction equation

HRID 917981 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]2[O:17][CH2:18][O:19][C:14]2=[CH:13][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(OC)(O[CH3:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][O:1][C:2]1[CH:16]=[C:15]2[O:17][CH2:18][O:19][C:14]2=[CH:13][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 53806082HCID 53806082, compound

Product 1

HCID 54189322HCID 54189322, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Preparation of final product, 2-methoxy-4,5-methylenedioxy-cinnamylbenzene (MMCB): A mixture of 19 g. of 2-hydroxy-4,5-methylenedioxy-cinnamylbenzene, 18.9 g. of dimethyl sulfate, 30.0 g. of anhydrous potassium carbonate, and 200 ml. of acetone was refluxed for 2 hrs. The mixture was then concentrated, diluted with 1% aqueous sodium hydroxide (200 ml.), and cooled. The oil which formed was extracted with ethyl ether. The ether was removed by evaporation and the residue was distilled to give MMCB (17.5 g.), b.p. 180° C at 0.25 mm. (Found: C, 75.9; H, 5.94. Calc. for C17H16O3 : C, 76.1; H, 6.01). The 100 Hz NMR spectrum of MMCB in deuterated chloroform exhibited a doublet (2 protons) at δ 3.44 (J = 6.0 Hz), a singlet (3 protons) at δ 3.74, a singlet (2 protons) at δ 5.85, a multiplet (2 protons) at δ 6.13-6.37, a singlet (1 proton) at δ 6.51, a singlet (1 proton) at δ 6.68, and a multiplet (5 protons) at δ 7.10-7.40.

Workup

  1. additionA mixture of 19 g
  2. concentrationThe mixture was then concentrated
  3. additiondiluted with 1% aqueous sodium hydroxide (200 ml.)
  4. temperaturecooled
  5. customThe oil which formed
  6. extractionwas extracted with ethyl ether
  7. customThe ether was removed by evaporation
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-6d133ac7550b43ad82503a822fe93070
Source dataset
uspto-grants-1976_07
Patent number
US03968234

Reaction notes

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