Dichloroacetic Acid → HCID 21568148, compound

HRID 1579219Notes

Reaction equation

HRID 1579219 reaction equation
[CH2:1]([C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([CH3:17])[CH:11]=1)[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.Cl[CH:19](Cl)[C:20]([OH:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH3:17][C:12]1[CH:13]=[CH:14][C:15]2[O:16][CH:19]([C:20]([OH:22])=[O:21])[O:8][C:7]3[CH:6]=[CH:5][C:4]([CH3:9])=[CH:3][C:2]=3[CH2:1][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6597Dichloroacetic Acid2×HCID 11430Potassium CarbonateHCID 76715Phenol, 2,2'-methylenebis[4-methyl-

Product 1

HCID 21568148HCID 21568148, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 27.4 g (0.120 mole) of 2,2'-methylene bis-p-cresol, 15.5 g (0.120 mole) of dichloroacetic acid, 66.5 g (0.480 mole) of potassium carbonate and 500 ml of isopropyl alcohol was refluxed for 24 hours with vigorous stirring after which 15.5 g. (0.120 mole) of dichloroacetic acid was added and the mixture was refluxed with stirring for 64 hours. The isopropyl alcohol was removed by distillation and replaced with 500 ml of water. The precipitate was collected, washed with 2% aqueous potassium hydroxide, suspended in 1 liter of water, and the suspension was acidified to litmus with 10% aqueous HCl. The resulting precipitate was collected and dried affording 2,10-dimethyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic acid, m.p. 200°-205°C (dec.).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture was refluxed
  3. stirringwith stirring for 64 hours
  4. customThe isopropyl alcohol was removed by distillation
  5. customThe precipitate was collected
  6. washwashed with 2% aqueous potassium hydroxide
  7. customThe resulting precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-e2801d6ec27a45bf86ac875e85942bff
Source dataset
uspto-grants-1976_01
Patent number
US03931173

Reaction notes

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