Chloroacetyl chloride → HCID 21391699, compound

HRID 461660Notes

Reaction equation

HRID 461660 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[Cl:24][CH2:25][C:26](Cl)=[O:27].C(=O)([O-])O.[Na+]>C(Cl)Cl.C1C=CC=CC=1>[Cl:24][CH2:25][C:26]([O:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[O:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:27]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21391683HCID 21391683, compound

Product 1

HCID 21391699HCID 21391699, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.58 g(5 m mol) of DL-α-hydroxy-4-(p-methoxybenzyloxycarbonyl)phenylacetic acid were suspended in 10 ml of anhydrous methylene chloride and ice-cooled. To this suspension were added dropwise 5 ml of anhydrous methylene chloride solution containing 0.68 g(6 m mol) of chloroacetyl chloride with stirring over the course of 5 minutes. Then the temperature of the solution was raised slowly to ambient temperature, and the solution was stirred for 30 minutes to give a clear solution, The reaction mixture was poured into 20 ml of ice-water and adjusted to pH 2.5 with an aqueous sodium hydrogen carbonate solution. The organic layer was separated and the aqueous layer was extracted several times with methylene chloride. The combined organic layers were washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give a pale yellow oily residue, which then was dissolved in 20 ml of benzene and left overnight in an ice-box, yielding 1.52 g (78%) of crystalline DL-α-chloroacetoxy-4-(p-methoxybenzyloxycarbonyl)phenylacetic acid of mp. 121°~125° C.

Workup

  1. temperatureice-cooled
  2. stirringthe solution was stirred for 30 minutes
  3. customto give a clear solution
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted several times with methylene chloride
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. customto give a pale yellow oily residue, which
  10. waitleft overnight in an ice-box

Sources & evidence

ORD record
ord-eba0e97955114594b2c73f8c91a86743
Source dataset
uspto-grants-1977_12
Patent number
US04064122

Reaction notes

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