Chloroform → HCID 14668265, compound

HRID 2255514Notes

Reaction equation

HRID 2255514 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[C:4]=1[C:5]([OH:7])=[O:6].C(Cl)(Cl)[Cl:17]>>[Cl:17][C:11]1[C:3]([O:2][CH3:1])=[C:4]([C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 6212Chloroform2×HCID 6114002,3,6-Trimethoxybenzoic acid

Product 1

HCID 14668265HCID 14668265, compoundYield 95%

Conditions

Temperature
0 °C

Procedure

2,5,6-trimethoxybenzoic acid 5.0 g (0.024 mol) was suspended in 75 ml of CHCl3 and cooled to 0° C. 1.9 ml (0.024 mol) of SO2Cl2 was added under N2 -atm. The reaction was stirred for 2 hr and allowed to slowly attain room temperature. The reaction mixture was diluted 100 ml CHCl3 and washed with 200 ml H2O. The aqueous layer was washed with 50 ml CHCl3 and the combined organic layer was dried (Na2SO4) and the solvent was evaporated. Gave 5.5 g (95%) of 3-chloro-2,5,6-trimethoxybenzoic acid (oil). Mw: 246.7.

Workup

  1. customallowed to slowly attain room temperature
  2. washwashed with 200 ml H2O
  3. washThe aqueous layer was washed with 50 ml CHCl3
  4. dry with materialthe combined organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-df260541073a4908ad097bee9561f127
Source dataset
uspto-grants-1993_08
Patent number
US05240957

Reaction notes

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