Hydrochloric Acid → HCID 21468306, compound

HRID 274174Notes

Reaction equation

HRID 274174 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]([O:21][CH2:22][CH2:23][CH3:24])[CH3:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].Cl>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]([O:21][CH2:22][CH2:23][CH3:24])[CH3:20])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21468285HCID 21468285, compound

Product 1

HCID 21468306HCID 21468306, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.6 g (8 mM) of the thus-obtained (-)-4-acetoxy-4'-(3-propoxybutyl)biphenyl was dissolved in 50 ml of methanol, added thereto with 10 ml of 20% NaOH aqueous solution, and then stirred at room temperature for 2 hrs. After completion of the reaction, the reaction mixture was made to pH 2-3 by adding 1N hydrochloric acid, and then further added thereto with 100 ml of ethyl acetate, and thereafter subjected to extraction treatment. The resulting organic layer was water-washed, and then concentrated under a reduced pressure to obtain 2.3 g of 4-hydroxy-4'-(3-propoxybutyl)biphenyl (V-47) with 100% yield [[α]D20 =-9.4° (C=1, CHCl3), nD20 =1.3462.

Workup

  1. additionadded
  2. customAfter completion of the reaction
  3. additionfurther added
  4. extractionwith 100 ml of ethyl acetate, and thereafter subjected to extraction treatment
  5. washwashed
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-a10cd81c4f604c04aea0c196a4b1e905
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Reaction notes

Loading…