Hydrochloric Acid → HCID 14496321, compound

HRID 704161Notes

Reaction equation

HRID 704161 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14](OCCC)[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:20][OH:21].[OH-:22].[Na+].Cl>O>[CH2:20]([O:21][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([OH:22])[CH3:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 14533191HCID 14533191, compound

Product 1

HCID 14496321HCID 14496321, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.45 g (0.01 mol) of unreacted ester (-)-4-benzyloxy-4'-(1-acetoxyethyl)biphenyl obtained in Example 12 was added into a mixture of 50 ml of methanol and 25 ml of a 20% sodium hydroxide solution and stirred at 30°-40° C. for 2 hours. The reaction mixture was added with 200 ml of water, adjusted to pH 4 with 4N hydrochloric acid and extracted with 500 ml of ether. The organic layer was washed with water and concentrated under reduced pressure to give 3.0 g (99% yield) of (-)-4-benzyloxy-4'-(1-hydroxyethyl)biphenyl as a white solid. By using 1.22 g (4 mmol) of this product as starting material, the alkylation, debenzylation and after-treatments of Example 19 were carried out to obtain 0.47 g (91% yield) of (-)-4-hydroxy-4'-(1-(2s-methylbutyloxy)ethyl)biphenyl. nD20 =1.5479, [α]D20 = -60.0° (c=1, CHCl3).

Workup

  1. extractionextracted with 500 ml of ether
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1dd595274261431caf04bf54452fdf2a
Source dataset
uspto-grants-1991_01
Patent number
US04985590

Reaction notes

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