4-Hydroxybenzoic Acid → 4-[(10-Hydroxydecyl)oxy]benzoic acid

HRID 1590012Notes

Reaction equation

HRID 1590012 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].[OH-].[K+].Cl>O.[I-].[K+].C(O)C>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1235261-Decanol, 10-chloro-

Product 1

HCID 197689544-[(10-Hydroxydecyl)oxy]benzoic acidYield 58%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxybenzoic acid (69.0 g, 0.5 mol), 10-chloro-1-decanol (106 g, 0.55 mol), potassium hydroxide (75 g, 1.15 mol), potassium iodide (0.1 g), and absolute ethanol (300 mL) was heated to reflux with mechanical stirring for 18 hours. The mixture was diluted with water (800 mL) and stirred 0.5 hours at room temperature. The mixture was acidified with 12N hydrochloric acid (125 mL) and the mixture stirred for 5 hours. The material was allowed to sit overnight and filtered. The solid was washed with water and air dried 4 days. The solid was recrystallized from tetrahydrofuran (300 mL) to give 4-(10-hydroxydecyloxy)benzoic acid (85.2 g, 58%): mp 115°-117° C.; NMR (CDCl3+d6 DMSO) 7.93(d, 2H), 6.85(d, 2H), 4.0(t, 2H), 3.52(t, 2H), 3.48(bs, 1H), 1.9-1.2(m, 16H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. stirringstirred 0.5 hours at room temperature
  4. stirringthe mixture stirred for 5 hours
  5. waitto sit overnight
  6. filtrationfiltered
  7. washThe solid was washed with water and air
  8. customdried 4 days
  9. customThe solid was recrystallized from tetrahydrofuran (300 mL)

Sources & evidence

ORD record
ord-f9bfa2796d754d86981887537310de1f
Source dataset
uspto-grants-1993_04
Patent number
US05202053

Reaction notes

Loading…