Hydrochloric Acid → HCID 20306115, compound

HRID 2419331Notes

Reaction equation

HRID 2419331 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[O:11]1[CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12]1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1[CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 90251,3-DimethoxybenzeneHCID 150362-Butyloxirane

Product 1

HCID 20306115HCID 20306115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
3 °C

Procedure

To a stirred, 5° C mixture of m-dimethoxybenzene 27.6g (0.20 mole), anhydrous stannic chloride 52.1g (0.20 mole) and 200 ml of methylene chloride which is constantly swept with nitrogen, is added dropwise, 1,2-epoxyhexane, 20.0g (0.20 mole) in 50 ml of methylene chloride. The exothermic reaction temperature is maintained at 3° C by the rate of addition. After the addition is complete, the reaction is stirred at 5° C for 30 minutes, at which time it is poured into iced concentrated hydrochloric acid. The layers are separated and the aqueous layer is extracted with methylene chloride. The combined organic layers are washed with water followed by 5% sodium bicarbonate solution and finally water. The last water wash is neutral to pH paper. The methylene chloride solvent is removed on a rotary evaporator at 40° C bath temperature. This residue is then fractionally distilled in vacuo. The third fraction, 140°-142° C/0.2 mm, is shown by nmr and ir to be the desired product. The yield is 25.32g (55%, theory).

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with methylene chloride
  5. washThe combined organic layers are washed with water
  6. washThe last water wash
  7. customThe methylene chloride solvent is removed on a rotary evaporator at 40° C bath temperature
  8. distillationThis residue is then fractionally distilled in vacuo
  9. customThe third fraction, 140°-142° C/0.2 mm

Sources & evidence

ORD record
ord-ac816e9a8ae4406a9da100eaa92e9ff9
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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