Dimethylformamide → 1-Hydroxy-3-[4-(tetradecyloxy)phenyl]-2-propanone

HRID 235689

Reaction equation

HRID 235689 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=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][CH3:14].CN(C)[CH:28]=[O:29].C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[OH:29][CH2:28][C:23](=[O:25])[CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][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][CH3:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10472964p-Tetradecyloxyphenylacetic acid

Product 1

HCID 202191091-Hydroxy-3-[4-(tetradecyloxy)phenyl]-2-propanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of about 60.0 g of (4-tetradecyloxyphenyl)acetic acid in about 400 ml of methylene chloride containing about 0.63 ml of dimethylformamide was added, over about 10 minutes about 27.31 g of oxalyl chloride. After about 2 hours the solvent was removed, the residue was dissolved in hexane and filtered through celite. The solvent was removed and the residue dried in vacuo. An about 110.82 g portion of tris-trimethylsilyloxyethylene was added and the solution was heated at about 95° C., under argon, for about 5 hours. The solution was poured into a mixture of about 30 ml of concentrated hydrochloric acid (about 12N) about 170 ml of water and about 200 ml of tetrahydrofuran with stirring and heat. This mixture was refluxed about 10 minutes, ethyl acetate was added, the warm organic layer separated and washed with brine, saturated sodium bicarbonate solution, then brine, dried and the solvent removed, giving, after recrystallization from hexane, about 52 g of the desired title compound as a white solid, mp. 84°-85° C.

Workup

  1. customAfter about 2 hours the solvent was removed
  2. dissolutionthe residue was dissolved in hexane
  3. filtrationfiltered through celite
  4. customThe solvent was removed
  5. customthe residue dried in vacuo
  6. additionAn about 110.82 g portion of tris-trimethylsilyloxyethylene was added
  7. additionThe solution was poured into a mixture of about 30 ml of concentrated hydrochloric acid (about 12N) about 170 ml of water and about 200 ml of tetrahydrofuran
  8. temperatureheat
  9. temperatureThis mixture was refluxed about 10 minutes
  10. additionethyl acetate was added
  11. customthe warm organic layer separated
  12. washwashed with brine, saturated sodium bicarbonate solution
  13. dry with materialbrine, dried
  14. customthe solvent removed
  15. customgiving
  16. customafter recrystallization from hexane, about 52 g of the desired title compound as a white solid, mp. 84°-85° C.

Sources & evidence

ORD record
ord-4da355b1c1e34f2496e38f104615b413
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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