4-Hydroxybenzoic Acid → 4-(6-Hydroxyhexyloxy)benzoic acid

HRID 1655816Notes

Reaction equation

HRID 1655816 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20]>>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 14797Potassium HydroxideHCID 779706-Bromo-1-hexanol

Product 1

HCID 36284134-(6-Hydroxyhexyloxy)benzoic acidYield 57%

Procedure

5.4 g of p-hydroxybenzoic acid was added to ethanol-dioxane mixture solvent, and an aqueous solution containing 6.6 g of potassium hydroxide was added thereto, followed by dropwise addition of 7.9 g of 6-bromohexanol and 12 hours of heat refluxing. The reaction mixture was then acidified, extracted with ethyl acetate and purified by column chromatography to obtain 5.3 g of the product (Yield: 57 %).

Workup

  1. additionwas added
  2. temperatureof heat
  3. temperaturerefluxing
  4. extractionextracted with ethyl acetate
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-0e7fc83b0ce24aa9b7afbc73f9ef68d8
Source dataset
uspto-grants-1993_10
Patent number
US05252251

Reaction notes

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