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

HRID 1460926Notes

Reaction equation

HRID 1460926 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 h. The mixture was diluted with water (800 mL) and stirred 0.5 h at room temperature. The mixture was acidified with 12N hydrochloric acid (125 mL) and the mixture stirred for 5 h. 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 +d6DMSO) 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 h at room temperature
  4. stirringthe mixture stirred for 5 h
  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-b92e0395dd9344a1b3fcbfa11ed4fcf1
Source dataset
uspto-grants-1991_12
Patent number
US05073294

Reaction notes

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