Chloroacetic Acid → HCID 13576589, compound

HRID 2164327Notes

Reaction equation

HRID 2164327 reaction equation
S(=O)(=O)(O)O.[Cl:6][CH2:7][C:8]([OH:10])=[O:9].[C:11](=[O:14])([O-])[O-].[K+].[K+].[C:17]1(C)[CH:22]=CC=[CH:19][CH:18]=1>>[O:14]1[CH2:11][CH2:19][CH2:18][CH2:17][CH:22]1[O:9][C:8](=[O:10])[CH2:7][Cl:6]

Participants

5

Reactant 4

HCID 300Chloroacetic Acid3×HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 11430Potassium Carbonate

Product 1

HCID 13576589HCID 13576589, compoundYield 100%

Procedure

A mixture of 185 g (2.2 mol) 3,4-dihydro-2H-pyrene, 200 ml toluene and 0.2 ml concentrated sulfuric acid is added dropwise over a period of 15 min at a temperature of 15° C. with a solution of 142 g (1.5 mol) chloroacetic acid in 500 ml toluene. During the addition ice-cooling is provided. After finishing the addition of the chloroacetic acid solution the reaction mixture is stirred 2 hours at room temperature. 15 g anhydrous potassium carbonate are added for stabilizing purposes. The reaction mixture thus stabilized then is evaporated in a rotating evaporator at 45° C. applying the vacuum of a water-jet vacuum pump. Having thus stripped off the lower boiling volatile components a mixture of the tetrahydropyranyl ester and potassium carbonate in an amount of 283 g is obtained as a residue. Based on the chloroacetic acid the yield is 100%.

Workup

  1. additionDuring the addition ice-
  2. temperaturecooling
  3. customis provided
  4. customThe reaction mixture thus stabilized then is evaporated in a rotating evaporator at 45° C.
  5. additiona mixture of the tetrahydropyranyl ester and potassium carbonate in an amount of 283 g
  6. customis obtained as a residue

Sources & evidence

ORD record
ord-a3652bb7454d4bbbaf193a2e8afb8e84
Source dataset
uspto-grants-1985_03
Patent number
US04503237

Reaction notes

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