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

HRID 1030346Notes

Reaction equation

HRID 1030346 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 4.1 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 4.1 g

Sources & evidence

ORD record
ord-3bc3d52dc8c844d4896c75c6b32da50c
Source dataset
uspto-grants-1992_04
Patent number
US05105017

Reaction notes

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