Sulfuric Acid → HCID 18992045, compound

HRID 375734Notes

Reaction equation

HRID 375734 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([C:8]([CH2:12][CH2:13][CH3:14])=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:16][C:17]([Cl:21])([Cl:20])[CH2:18]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([C:8]([CH2:12][CH2:13][CH3:14])=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH2:18][C:17]([Cl:21])([Cl:20])[Cl:16])=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8259TrichloroethanolHCID 18992061HCID 18992061, compound

Product 1

HCID 18992045HCID 18992045, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 g of 3,5-dihydroxy-2-methyl-6-propyl benzoic acid, 4.48 g of 2,2,2-trichloroethanol, and 0, 1 ml of 98% sulfuric acid in 40 ml of toluene was heated at reflux for 3 hours, water being constantly removed by a Dean-Stark trap. The mixture was cooled, diluted with 80 ml of ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. Chromatography of the residue on silica gel using acetone/hexane (1:6, v/v) as eluent afforded 7.1 g of 2,2,2-trichloroethyl 3,5-dihydroxy-2-methyl-6-propylbenzoate as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customwater being constantly removed by a Dean-Stark trap
  4. temperatureThe mixture was cooled
  5. additiondiluted with 80 ml of ethyl acetate
  6. washwashed with brine
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e50ff80804004614869a50ae429c772f
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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