Hydrochloric Acid → HCID 13366425, compound

HRID 1632467Notes

Reaction equation

HRID 1632467 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].Cl.C=O.CO[CH2:20][Cl:21]>O.C(O)(=O)C>[F:14][C:11]([F:12])([F:13])[O:10][C:3]1[CH:4]=[C:5]([CH3:9])[C:6]([CH2:20][Cl:21])=[C:7]([CH3:8])[C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7864Chloromethyl Methyl EtherHCID 13366424HCID 13366424, compound

Product 1

HCID 13366425HCID 13366425, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 31.5 (0.15 mol) of 2,3,5-trimethyl-1-trifluoromethoxybenzene, 315 ml of acetic acid, 31.5 ml of concentrated hydrochloric acid, 31.5 ml of aqueous formaldehyde and 13 g (0.185 mol) of chloromethyl methyl ether was heated to 85° C. for 72 hours. (Small samples were worked up periodically after 48 hours to optimize the ratio of monochloromethyl product:dichloromethyl product:starting material). The solution was then cooled, poured into 1.5 liters of water and extracted with 3×500 ml of hexane. The hexane extracts were washed with 1 liter of water and 500 ml of saturated NaHCO3 solution, dried (MgSO4), filtered, and concentrated to give 30 g of crude (4-trifluoromethoxy 2,3,6-trimethylphenyl)methyl chloride containing some starting material, 2,3,5-trimethyl-1-trifluoromethoxybenzene, which was removed by distillation at 24°-30° C./0.05 mm. The residue (22 g), crude (4-trifluoromethoxy-2,3,6-trimethylphenyl)methyl chloride, was used directly in the next step.

Workup

  1. customperiodically after 48 hours
  2. temperatureThe solution was then cooled
  3. extractionextracted with 3×500 ml of hexane
  4. washThe hexane extracts were washed with 1 liter of water and 500 ml of saturated NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10845c27a7b743a5a1b12a21b700a769
Source dataset
uspto-grants-1984_10
Patent number
US04476056

Reaction notes

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