Hydrochloric Acid → HCID 20306146, compound

HRID 1732388Notes

Reaction equation

HRID 1732388 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:2]1.Cl.[C:9]1([CH3:16])[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1>>[CH3:16][C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][C:14]=1[CH:3]([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:2][OH:1]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7929M-Xylene3×HCID 150362-Butyloxirane

Product 1

HCID 20306146HCID 20306146, compound

Conditions

Temperature
3 °C

Procedure

To a stirred, 0° C. mixture of m-xylene 173 g (1.63 mole) and anhydrous stannic chloride 78.0 g (0.30 mole) which is constantly swept with nitrogen, is added dropwise, 1,2-epoxyhexane, 30.0 g (0.30 mole) in 50 g m-xylene. The exothermic temperature is maintained at 3° C. by the rate of addition. After the addition is completed, the reaction which now contains 223 g (2.0 mole) m-xylene is stirred for 30 minutes at 0° C. then poured into iced concentrated hydrochloric acid. The aqueous and organic layers are separated. After extracting the aqueous portion with ethyl ether, this organic layer is combined with the previous organic fraction. This combined organic material is washed successively with water, sodium bicarbonate and again water. The dried organic solvent mixture of ethyl ether and excess unreacted m-xylene is then removed on rotary evaporator. The concentrated residue is fractionally distilled in vacuo. The third fraction, 112° C./0.5 mm, is shown to be the desired product by spectral and analytical data. The yield is 35.6 g (57.6% theory).

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. customThe aqueous and organic layers are separated
  4. extractionAfter extracting the aqueous portion with ethyl ether
  5. washThis combined organic material is washed successively with water, sodium bicarbonate and again water
  6. additionThe dried organic solvent mixture of ethyl ether and excess unreacted m-xylene
  7. customis then removed on rotary evaporator
  8. distillationThe concentrated residue is fractionally distilled in vacuo
  9. customThe third fraction, 112° C./0.5 mm

Sources & evidence

ORD record
ord-743ecf5795e540bca8bbbee450bbe5ac
Source dataset
uspto-grants-1980_12
Patent number
US04237158

Reaction notes

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