Hydrochloric Acid → 4'-Decyloxybiphenyl-4-carboxylic Acid

HRID 1417

Reaction equation

HRID 1417 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[K+].[I-].[Na+].Cl>O.C(O)C>[CH2:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 81731-BromodecaneHCID 14797Potassium Hydroxide2×HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 114510854'-Decyloxybiphenyl-4-carboxylic AcidYield 6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 21.4 g (0.1 mol) of 4'-hydroxybiphenyl-4-carboxylic acid, 33.15 g (0.15 mol) of n-decyl bromide, 13.20 g (0.2 mol) of 85% potassium hydroxide, 1.05 g (7 mmol) of sodium iodide, 500 ml of ethanol and 100 ml of distilled water was heated under reflux at 100° C. for 12 hours. After 40 ml of 25% potassium hydroxide was added, the mixture was further heated under reflux for 2 hours. After allowing the reaction system to cool up to room temperature, the reaction mixture in cold water was acidified with 36% hydrochloric acid. The deposited product was separated by filtration and dissolved in acetone with heating, followed by filtration. The resulting filtrate was concentrated to obtain 1.97 g (6 mmol) of 4'-decyloxybiphenyl-4-carboxylic acid.

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was further heated
  3. temperatureunder reflux for 2 hours
  4. temperatureto cool up to room temperature
  5. customThe deposited product was separated by filtration
  6. dissolutiondissolved in acetone
  7. temperaturewith heating
  8. filtrationfollowed by filtration
  9. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-0396fca3395e4ebeb8f2c15f2dea83c8
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Linked notes

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