Thionyl Chloride → HCID 54233952, compound

HRID 1679612Notes

Reaction equation

HRID 1679612 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]2[CH2:10][CH:6]([C:7]2([CH3:12])[CH3:11])[CH:5]1[CH3:13])(O)=[O:2].S(Cl)([Cl:16])=O>CO>[CH:6]12[CH2:10][CH:8]([C:7]1([CH3:12])[CH3:11])[CH2:9][CH:4]([C:1]([Cl:16])=[O:2])[CH:5]2[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53510964284-84-0

Product 1

HCID 54233952HCID 54233952, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15 g of (+)-3-carboxypinane of optical rotation [α]D25 = +20.2° (c = 1, CH3OH) are boiled with excess thionyl chloride under reflux in the absence of moisture, until the evolution of gas has ceased. The excess thionylchloride is then distilled, followed by the acid chloride boiling at from 62° to 64° C/0.08 mm Hg and having an optical rotation of [α]D24 = +28.1° (pure).

Workup

  1. temperatureunder reflux in the absence of moisture, until the evolution of gas
  2. distillationThe excess thionylchloride is then distilled
  3. customfollowed by the acid chloride boiling at from 62° to 64° C/0.08 mm Hg

Sources & evidence

ORD record
ord-3dedf7450e5741488301ba1d57abe660
Source dataset
uspto-grants-1978_03
Patent number
US04081477

Reaction notes

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