1,4-Butanediol → 4-(4-Acetyl-3-hydroxy-2-propylbenzyloxy)-1-butanol

HRID 275380Notes

Reaction equation

HRID 275380 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][OH:7].[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[C:14]([CH2:20][CH2:21][CH3:22])[C:13]=1[OH:23])(=[O:11])[CH3:10]>O>[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:8])=[C:14]([CH2:20][CH2:21][CH3:22])[C:13]=1[OH:23])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chloride

Product 1

HCID 156826844-(4-Acetyl-3-hydroxy-2-propylbenzyloxy)-1-butanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 9.6 g. of a 50% oil dispersion of sodium hydride in 100 ml. of 1,4-butanediol were added 11.3 g. of 4-acetyl-3-hydroxy-2-propylbenzyl chloride. The reaction was stirred overnight at room temperature and then heated to 60° C. for six hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate solution was evaporated to dryness and the residue was purified by chromatography over silica gel to provide 14.1 g. of the desired title product. NMR.

Workup

  1. additionTo a suspension of 9.6 g
  2. temperatureheated to 60° C. for six hours
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate solution was evaporated to dryness
  5. customthe residue was purified by chromatography over silica gel
  6. customto provide 14.1 g

Sources & evidence

ORD record
ord-68c5ffadd61c4ec5a76950b5b0c3c717
Source dataset
uspto-grants-1995_02
Patent number
US05393768

Reaction notes

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