Oxalyl chloride → HCID 20219627, compound

HRID 235693Notes

Reaction equation

HRID 235693 reaction equation
[CH2:1]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27]([OH:29])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)(=O)[C:31](Cl)=[O:32]>C(Cl)Cl>[OH:32][CH2:31][C:27](=[O:29])[CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 20218511HCID 20218511, compound

Product 1

HCID 20219627HCID 20219627, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of about 50 g of 2-(octadecyloxy)phenyl acetic acid in about 400 ml of methylene chloride was added about 19.6 g of oxalylchloride. After stirring about 3 hours the solvent was removed and the residue was dissolved in hexane and filtered through celite. The hexane was removed and to the residue was added about 79.5 g of tris-trimethylsilyloxyethylene. This mixture was stirred at about 90°-95° C. for 1.5 hours, then the oil was poured into a mixture of about 30 ml of concentrated (about 12N) hydrochloric acid, about 170 ml of water and about 200 ml of tetrahydrofuran and stirred at reflux for about 1/2 hour. The tetrahydrofuran was removed and the residue was extracted with ether. The ether extract was washed with dilute sodium bicarbonate, then brine and dried. The solvent was removed and the residue recrystallized from hexane, giving about 31 g of the desired title compound as a white solid, mp 59°-60° C.

Workup

  1. customwas removed
  2. dissolutionthe residue was dissolved in hexane
  3. filtrationfiltered through celite
  4. customThe hexane was removed and to the residue
  5. additionwas added about 79.5 g of tris-trimethylsilyloxyethylene
  6. stirringThis mixture was stirred at about 90°-95° C. for 1.5 hours
  7. additionthe oil was poured into a mixture of about 30 ml
  8. concentrationof concentrated (about 12N) hydrochloric acid, about 170 ml of water and about 200 ml of tetrahydrofuran
  9. stirringstirred
  10. temperatureat reflux for about 1/2 hour
  11. customThe tetrahydrofuran was removed
  12. extractionthe residue was extracted with ether
  13. extractionThe ether extract
  14. washwas washed with dilute sodium bicarbonate
  15. dry with materialbrine and dried
  16. customThe solvent was removed
  17. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-6082c6eae73b4032acd65cb104175251
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

Loading…