Dichloroacetic Acid → HCID 69820753, compound

HRID 1265310Notes

Reaction equation

HRID 1265310 reaction equation
C(O[C@@H]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)OC1(CC1C=CC=CC=1)O)C1C=CC=CC=1.Cl[CH:49](Cl)[C:50]([OH:52])=[O:51]>[Cl-].C[N+](C)(C)C.C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:25]([O:24][C@@H:49]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:52][CH:50]1[O:51][CH2:14][CH2:15][OH:16])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 6597Dichloroacetic AcidHCID 131723848HCID 131723848, compound

Product 1

HCID 69820753HCID 69820753, compound

Reagents, catalysts & solvents 3

HCID 6379Tetramethylammonium chlorideCatalystHCID 1140TolueneSolvent3×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture that consists of 54.1 g (100 mmol) of 2,3,4,6-tetra-O-benzyl-benzylgalactopyranose, 1.64 g (15 mmol) of tetramethylammonium chloride in 350 ml of toluene and 200 ml of 60% aqueous sodium hydroxide solution is cooled to 0° C. At 0° C., 52.7 g (130 mmol) of 2-(4,4′-dimethoxytriphenylmethyloxy)-ethylbromide, dissolved in 100 ml of toluene, is added in drops over 30 minutes while being stirred vigorously. It is stirred for three hours at 0° C. 300 ml of toluene is added, the organic phase is separated, and the aqueous phase is extracted twice with 200 ml of toluene. The solvent is distilled off in a vacuum. The residue is taken up in 500 ml of dichloromethane, and 25 g (194 mmol) of dichloroacetic acid is added. It is stirred for three hours at 35° C. The solution is washed three times with 300 ml of 10% aqueous sodium hydroxide solution, and the organic phase is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1).

Workup

  1. additionis added in drops over 30 minutes
  2. stirringIt is stirred for three hours at 0° C
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted twice with 200 ml of toluene
  5. distillationThe solvent is distilled off in a vacuum
  6. stirringIt is stirred for three hours at 35° C
  7. washThe solution is washed three times with 300 ml of 10% aqueous sodium hydroxide solution
  8. customthe organic phase is evaporated to the dry state
  9. customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1)

Sources & evidence

ORD record
ord-8c4156f2ee324248b7de50c64681fd48
Source dataset
uspto-grants-2003_04
Patent number
US06545135B2

Reaction notes

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