Thionyl Chloride → HCID 10355913, compound

HRID 1246326Notes

Reaction equation

HRID 1246326 reaction equation
[CH2:1]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][C:7]=1[O:17][CH3:18])[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:9]([C:10]([Cl:21])=[O:11])=[CH:8][C:7]=1[O:17][CH3:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 104450144-Butoxy-3,5-dimethoxybenzoic acid

Product 1

HCID 10355913HCID 10355913, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-butyloxy-3,5-dimethoxybenzoic acid (5.0 g, 0.0197 mol) and thionyl chloride (10 mL) in toluene (10 mL) was heated at 90° C. for 18 h. The reaction mixture was concentrated under reduced pressure. To remove excess of thionyl chloride the residue was repeatedly redissolved in toluene (3×20 mL) and the resulting solution evaporated to dryness to obtain 4-butyloxy-3,5-dimethoxybenzoyl chloride (5.3 g, 99% yield) as a pale yellow oil. 1H NMR (CDCl3) δ: 0.99 (t, J=5.0 Hz, 3H), 1.47 (m, 2H), 1.73 (m, 2H), 3.90 (s, 6H), 4.09 (t, J=5.1 Hz, 2H), 7.36 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo remove excess of thionyl chloride the residue
  3. dissolutionwas repeatedly redissolved in toluene (3×20 mL)
  4. customthe resulting solution evaporated to dryness

Sources & evidence

ORD record
ord-725d6d35313e44d6b0d697ffd54a8665
Source dataset
uspto-grants-2006_10
Patent number
US07126027B2

Reaction notes

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