Hydrochloric Acid → HCID 14496323, compound

HRID 327868Notes

Reaction equation

HRID 327868 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([OH:23])[CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](Cl)(=[O:26])[CH3:25].Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]([O:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14496321HCID 14496321, compound

Product 1

HCID 14496323HCID 14496323, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.09 g (20 mmol) of (+)-4-benzyloxy-4'-(1-hydroxyethyl)biphenyl was dissolved in 100 ml of dry pyridine, followed by dropwise addition of 1.73 g (22 mmol) of acetyl chloride. The mixture was stirred at room temperature for one hour, then poured into 1 liter of 2N hydrochloric acid and extracted with 300 ml of toluene. The toluene layer was washed with water, then with a 7% sodium bicarbonate solution and again with water successively in that order and then dried over anhydrous magnesium sulfate. This toluene solution was distilled under reduced pressure to remove the solvent and the residual white solid was purified by column chromatography packed with 200 g of silica gel to obtain 6.86 g of (+)-4-benzyloxy-4'-(1-acetoxyethyl)biphenyl in a 99% yield. It was further purified by recrystallization from ethanol. [α]D25 =+56.3° (c=1, CHCl3); melting point: 137° C.

Workup

  1. extractionextracted with 300 ml of toluene
  2. washThe toluene layer was washed with water
  3. dry with materialwith a 7% sodium bicarbonate solution and again with water successively in that order and then dried over anhydrous magnesium sulfate
  4. distillationThis toluene solution was distilled under reduced pressure
  5. customto remove the solvent
  6. customthe residual white solid was purified by column chromatography

Sources & evidence

ORD record
ord-addbbd292f3f4a1e861f29d110548795
Source dataset
uspto-grants-1993_12
Patent number
US05274168

Reaction notes

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