Glycolic Acid → HCID 20096274, compound

HRID 1769935Notes

Reaction equation

HRID 1769935 reaction equation
ClC[C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:17]([OH:21])(=[O:20])[CH2:18][OH:19]>C(#N)C>[C:17]([O:21][C:3]1[C:16]2[C:11]([CH:10]=[C:9]3[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]3)=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:20])[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 323859-(Chloromethyl)anthracene

Product 1

HCID 20096274HCID 20096274, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of 9-chloromethyl anthracene (1.0 g, 4.4 mmol) in dry acetonitrile (50 ml) is added to a solution of glycolic acid (0.71 g 18.8 mmol) (dried by successive evaporation from dry acetonitrile) in acetonitrile (10 ml). The reaction is stirred for 18 hours at room temperature and refluxed for 2 hours. After evaporation of acetonitrile the residue is redissolved in methylene chloride and extracted with water and 0.5M sodium bicarbonate. The solution is dried and solvent evaporated. The residue is recrystallized from refluxing benzene at 40° C. to yield 0.73 g (2.6 mmol) of yellow crystals.

Workup

  1. temperaturerefluxed for 2 hours
  2. customAfter evaporation of acetonitrile the residue
  3. dissolutionis redissolved in methylene chloride
  4. extractionextracted with water and 0.5M sodium bicarbonate
  5. customThe solution is dried
  6. customsolvent evaporated
  7. customThe residue is recrystallized
  8. temperaturefrom refluxing benzene at 40° C.

Sources & evidence

ORD record
ord-eb17687730da45e1b6e95498df97f44d
Source dataset
uspto-grants-1995_01
Patent number
US05384241

Reaction notes

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