Ethanol → 4-(Carboxybutyl)-4'-dodecyloxybiphenyl

HRID 36825Notes

Reaction equation

HRID 36825 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[K+].C(O)C.O>Cl>[C:30]([CH2:29][CH2:28][CH2:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=2)=[CH:21][CH:22]=1)([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 54101004HCID 54101004, compound

Product 1

HCID 542681554-(Carboxybutyl)-4'-dodecyloxybiphenylYield 90.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

19 mmol of the compound from Example 15, 66.7 mmol of KOH, 100 ml of ethanol and 50 ml of water are introduced into a 500 ml single-necked flask fitted with reflux condenser and magnetic stirrer, and the mixture is refluxed for 6 hours. After cooling, the reaction mixture is carefully acidified in concentrated HCl solution and subsequently washed with water until neutral. The solvent is stripped off, and the residue is recrystallized a number of times from glacial acetic acid. The residue is then boiled with methanol and subsequently with ether and filtered off with suction. Yield: 90.5%.

Workup

  1. customfitted
  2. temperaturewith reflux condenser and magnetic stirrer
  3. temperaturethe mixture is refluxed for 6 hours
  4. temperatureAfter cooling
  5. washsubsequently washed with water until neutral
  6. customthe residue is recrystallized a number of times from glacial acetic acid
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-8e75e78528e7419c91c7087c90cc5233
Source dataset
uspto-grants-1995_05
Patent number
US05417884

Reaction notes

Loading…