Thionyl Chloride → HCID 19869706, compound

HRID 330305Notes

Reaction equation

HRID 330305 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]O)[CH2:2][CH3:3].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][Cl:15])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 12194601(2-PROPOXYPHENYL)METHANOL

Product 1

HCID 19869706HCID 19869706, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent2×

Procedure

A 2 liter flask was charged with 316 grams (1.9 moles, 1.0 eg.) of 2-propoxybenzyl alcohol and 15 grams of pyridine (0.0126 moles) in 750 ml of toluene. 237 grams (1.99 moles, 1.01 ec.) of thionyl chloride was slowly added dropwise, allowing the reaction mixture to reflux during the addition. The reaction was stirred 4 hours at room temperature after which the toluene and thionyl chloride were removed under reduced pressure. To the remaining oil was added water and ether and washed with saturated NaHCO3 Drying and removal of the solvent gave 367 grams (100% yield) of a red oil.

Workup

  1. temperatureto reflux during the addition
  2. customwere removed under reduced pressure
  3. additionTo the remaining oil was added water and ether
  4. washwashed with saturated NaHCO3 Drying and removal of the solvent

Sources & evidence

ORD record
ord-1887c46c178047f4904870d84746ad48
Source dataset
uspto-grants-1990_01
Patent number
US04895865

Reaction notes

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