Sulfuric Acid → HCID 22177393, compound

HRID 1797339Notes

Reaction equation

HRID 1797339 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][Cl:12])=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 74243,5-Dihydroxybenzoic AcidHCID 748286-Chloro-1-hexanol

Product 1

HCID 22177393HCID 22177393, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.541 g (10.0 mmol) 3,5-dihyroxybenzoic acid, 2.732 g (20.0 mmol) 6-chlor-1-hexanol were dissolved in 20 ml toluene, and 0.2 ml of concentrated sulfuric acid was added thereto. The reaction mixture was then heated at reflux temperature for 20 hours, and was partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 120 g silica gel using cyclohexane:ethyl acetate (7:3) as eluant yielded 2.3 g (84%) of 6-chlorohexyl 3,5-dihydroxybenzoate as orange oil.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux temperature for 20 hours
  3. customwas partitioned between ethyl acetate
  4. washThe organic phase was washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-2e30cb01027e414bbcbbade34a716fe7
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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