Hydrochloric Acid → HCID 14745761, compound

HRID 2166000Notes

Reaction equation

HRID 2166000 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:19][C:20]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].C(Cl)Cl.Cl>N1C=CC=CC=1>[F:19][C:20]1[CH:28]=[C:27]([O:29][C:14](=[O:15])[C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:18][CH:17]=2)[CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 27602504-Octyloxybenzoyl chlorideHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 14745761HCID 14745761, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Octyloxybenzoic acid chloride (10.74 g) and 6.24 g of 2-fluoro-4-hydroxybenzoic acid were stirred in 20 ml of pyridine and 50 ml of methylene chloride for 3 hours on refluxing by heating. After the reaction mixture was left to cool, it was neutralized with 10% hydrochloric acid, and the precipitated crystals were separated by filtration, and washed with water and then with cold methanol. The resulting crude crystals were recrystallized from ethanol to obtain 12.11 g of 2-fluoro-4-(4-octyloxybenzoyloxy)benzoic acid (yield 78%) which was liquid crystalline (transition temperatures: m.p. 147° to 148° C., N-I point 217° C.).

Workup

  1. temperatureby heating
  2. waitAfter the reaction mixture was left
  3. temperatureto cool
  4. customthe precipitated crystals were separated by filtration
  5. washwashed with water
  6. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-76f8122e0da64256864c0df00673942f
Source dataset
uspto-grants-1990_07
Patent number
US04943386

Reaction notes

Loading…