Thionyl Chloride → HCID 12962152, compound

HRID 1156282Notes

Reaction equation

HRID 1156282 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10](O)[C:4]=2[CH:3]=1.S(Cl)([Cl:20])=O>CCOCC>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([Cl:20])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20215998HCID 20215998, compound

Product 1

HCID 12962152HCID 12962152, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

2-Chloro-11-hydroxy-6,11-dihydrodibenz[b,e]oxepin (12.75 g; 0.051 mole) is dissolved in dry ether (220 ml) and cooled to 5° C. under a dry nitrogen atmosphere. Thionyl chloride (6.76 g; 0.056 mole) in ether (20 ml) is slowly added dropwise while maintaining the temperature below 5° C. Upon completion of the addition, the reaction is brought to ambient temperature and stirred for three hours. Upon removal of the solvent in vacuo, the resulting solid is recrystallized from cyclohexane to give crystals of 2,11-dichloro-6,11-dihydrodibenz[b,e]oxepin, m.p. 125°-127° C.

Workup

  1. temperaturewhile maintaining the temperature below 5° C
  2. additionUpon completion of the addition
  3. customis brought to ambient temperature
  4. customUpon removal of the solvent in vacuo
  5. customthe resulting solid is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-34c66a6721234c46b2223aa4548d11c4
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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