Chloroacetic Acid → HCID 23036786, compound

HRID 1709774Notes

Reaction equation

HRID 1709774 reaction equation
[C:1]([C:10]1[CH:15]=[C:14]([C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[OH:25])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+].[Na].Cl[CH2:30][C:31]([OH:33])=[O:32].Cl>O.C1(C)C=CC=CC=1.CS(C)=O>[C:1]([C:10]1[CH:15]=[C:14]([C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[O:25][CH2:30][C:31]([OH:33])=[O:32])([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 760132,4-DicumylphenolHCID 5360545Sodium

Product 1

HCID 23036786HCID 23036786, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a 500 ml three neck flask equipped with mechanical stirrer, nitrogen inlet and Dean-Stark trap/ condenser was added 40.0 grams (0.121 moles) 2,4-dicumylphenol, 150 ml dimethylsulfoxide (DMSO), 0.121 moles of sodium hydroxide (9.68 grams of 50% aqueous NaOH), and 100 ml toluene. The mixture is stirred and heated to azeotropically remove water. After water removal is complete the temperature is lowered to about 90° C. and 14.10 grams (0.121 moles) of the sodium salt of chloroacetic acid is added. The reaction is stirred at 90° C. for 16 hours. The product is isolated by cooling and pouring the reaction mixture into 500 ml of a 2% aqueous hydrochloric acid. After filtration, washing with water and drying a white powder was obtained which exhibited a melting point of 114° C.

Workup

  1. customAfter water removal
  2. customis lowered to about 90° C.
  3. stirringThe reaction is stirred at 90° C. for 16 hours
  4. customThe product is isolated
  5. temperatureby cooling
  6. filtrationAfter filtration
  7. washwashing with water
  8. customdrying a white powder
  9. customwas obtained which

Sources & evidence

ORD record
ord-fbd05996680944f89e49c41d01e2e13c
Source dataset
uspto-grants-1990_08
Patent number
US04950782

Reaction notes

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