Thionyl Chloride → HCID 21565170, compound

HRID 1580120Notes

Reaction equation

HRID 1580120 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:12]O)[CH:3]=1.O=S(Cl)[Cl:16]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:12][Cl:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21565172HCID 21565172, compound

Product 1

HCID 21565170HCID 21565170, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 39.5 g (0.167 mole) portion of 2-bromo-5-(hydroxymethyl)-naphthalene in 300 ml of chloroform was treated at 0°-5° over 0.3 hours with 75 ml (123 g, 1.03 mole) of SOCl2. The reaction mixture was allowed to warm to room temperature over 0.5 hours, heated to reflux over 0.2 hours, and allowed to cool slowly to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was taken up in 150 ml of benzene and again concentrated under reduced pressure to give 43 g (100%) of a light yellow oil which crystallized, m.p. 73°-76°.

Workup

  1. temperatureheated
  2. temperatureto reflux over 0.2 hours
  3. temperatureto cool slowly to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. concentrationagain concentrated under reduced pressure

Sources & evidence

ORD record
ord-10e5b29377764eabbce7a57bc05aafb0
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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