4-Hydroxybenzyl Alcohol → HCID 11469652, compound

HRID 1844656Notes

Reaction equation

HRID 1844656 reaction equation
ClCCl.[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:13][Si:14](Cl)([CH3:16])[CH3:15].[Na+].[Cl-]>C(N(CC)CC)C>[CH3:13][Si:14]([CH3:16])([CH3:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 6397Chlorotrimethylsilane

Product 1

HCID 11469652HCID 11469652, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

300 ml of dichloromethane followed by 60 g of triethylamine are added to 30 g of 4-hydroxymethyl-phenol introduced into a 500 ml flask maintained under a hydrogen atmosphere. The temperature of the obtained solution is brought to 10° C. and 64 g of trimethylsilyl chloride are added thereto in about one hour, keeping the temperature at 10° C. Thus, the temperature is left to spontaneously rise to 25° C., maintaining such conditions for one hour. Then, the reaction of the substrate is controlled under TLC. Upon ascertaining the disappearance of the initial product, 200 ml of an aqueous saturated NaCl solution are added and the two-phase system is stirred vigorously for 10′ and then the two phases are decanted. The lower organic phase is washed with two 200 ml portions of deionised water and then concentrated to residue, obtaining a yellowish oil. Such residue is recovered using 500 ml of DMF in a 2-liter flask and a solution constituted by 3 g of Lithium acetate in 60 ml of water is added to the obtained solution. The mixture is maintained at 25° C. for one hour, then the removal of the trimethylsilyl group on the phenolic hydroxyl is controlled under TLC. Then, 650 ml of a saturated NaCl solution and 455 ml of toluene are added to the reaction mixture and the mixture is stirred vigorously for 10′, then the two phases are left to decant. The upper organic phase is then washed with two 650 ml portions of deionised water and concentrated under vacuum, obtaining 33 g of the desired product (70% yield).

Workup

  1. additionintroduced into a 500 ml flask
  2. temperaturemaintained under a hydrogen atmosphere
  3. customis brought to 10° C.
  4. customat 10° C
  5. waitThus, the temperature is left to spontaneously rise to 25° C.
  6. temperaturemaintaining such conditions for one hour
  7. customThen, the reaction of the substrate
  8. additionare added
  9. customare decanted
  10. washThe lower organic phase is washed with two 200 ml portions of deionised water
  11. concentrationconcentrated to residue
  12. customobtaining a yellowish oil
  13. customSuch residue is recovered
  14. additionis added to the obtained solution
  15. customthe removal of the trimethylsilyl group on the phenolic hydroxyl
  16. additionThen, 650 ml of a saturated NaCl solution and 455 ml of toluene are added to the reaction mixture
  17. stirringthe mixture is stirred vigorously for 10′, then the two phases
  18. waitare left
  19. customto decant
  20. washThe upper organic phase is then washed with two 650 ml portions of deionised water
  21. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01c6afd4b04e44fa9671535080b92c97
Source dataset
uspto-grants-2015_02
Patent number
US08946456B2

Reaction notes

Loading…