4-(Chloromethyl)phenylacetic acid → Phenylacetic Acid

HRID 437353Notes

Reaction equation

HRID 437353 reaction equation
ClC[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.O1CCN(NC(=S)[S-])CC1>CO>[C:6]1([CH2:9][C:10]([OH:12])=[O:11])[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 103134194-(Chloromethyl)phenylacetic acidHCID 21792278Morpholinodithiocarbamate

Product 1

HCID 999Phenylacetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.85 g (0.01 mole) of 4-chloromethylphenyl acetic acid and 6.25 g (0.025 mole) of freshly prepared morpholinodithiocarbamate salt in 250 ml of methanol was stirred under nitrogen for 20 hours at room temperature. The solvent was evaporated, water was added and the solution was acidified to pH 1 using aqueous 10% hydrochloric acid then extracted with ethylacetate, dried over anhydrous magnesium sulfate and evaporated. The residue was recrystallized from ethylacetate to give p-morpholinodithiocarbamatemethyl)phenylacetic acid. M.P. 163° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthen extracted with ethylacetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was recrystallized from ethylacetate

Sources & evidence

ORD record
ord-e96337b4aaed454dba47a3b07ac2578c
Source dataset
uspto-grants-1977_06
Patent number
US04031083

Reaction notes

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