Hydrochloric Acid → HCID 19387341, compound

HRID 2399336Notes

Reaction equation

HRID 2399336 reaction equation
[C:1]([C:4]([OH:26])([CH2:9][CH:10]([OH:25])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[CH2:5][C:6]([OH:8])=[O:7])(O)=[O:2].[Na][Na].Cl>O1CCCC1>[C:6]([CH2:5][C:4]1([OH:26])[CH2:9][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[O:25][C:1]1=[O:2])([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 141233DisodiumHCID 19387340HCID 19387340, compound

Product 1

HCID 19387341HCID 19387341, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ±(3R*, 5S*) 3-carboxy-11-(2,4-dichlorophenyl)-3,5-dihydroxyundecanoic acid, disodium salt (11.8 g, 25.1 mmol), aqueous HCl (3M, 200 ml), and tetrahydrofuran (200 ml) was heated at 60° C. for 6 h, then cooled. Most of the tetrahydrofuran was removed under vacuum. The residual mixture was diluted with water, and extracted with ether. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum, and the residue recrystallised (ether/petroleum ether 40°-60° C.) to give the title compound (8.80 g, 90%) as a white solid, m.p. 77°-79° C.

Workup

  1. temperaturecooled
  2. customMost of the tetrahydrofuran was removed under vacuum
  3. additionThe residual mixture was diluted with water
  4. extractionextracted with ether
  5. washThe extracts were washed with water, saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under vacuum
  8. customthe residue recrystallised (ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-e1915d568a9349ddac5c314190c30f10
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

Loading…