Water → HCID 68520095, compound

HRID 1870573Notes

Reaction equation

HRID 1870573 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[C:9](\[CH3:13])/[C:10]([OH:12])=[O:11].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23]O)[CH3:21])[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1CCCCC1.CCCCCC>[CH3:21][CH:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])[CH2:22][CH2:23][O:11][C:10](=[O:12])/[C:9](/[CH3:13])=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8842CitronellolHCID 18424859HCID 18424859, compound

Product 1

HCID 68520095HCID 68520095, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of 6.0 g of (E)-3-(2-hydroxy-phenyl)-2-methyl-acrylic acid, 5.3 g of citronellol and 1 g of p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed for 6.5 hours using a water separator. Then the reaction mixture was cooled down, diluted with hexane and washed to neutrality with saturated sodium bicarbonate and water. The organic phase was dried, filtered and evaporated to dryness. The resulting yellow oil was purified by chromatography to yield 6.45 g of a colourless oil.

Workup

  1. temperatureThen the reaction mixture was cooled down
  2. washwashed
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting yellow oil was purified by chromatography

Sources & evidence

ORD record
ord-720212eb51ab4ae6b588a247998dd5ed
Source dataset
uspto-grants-2000_08
Patent number
US06096918

Reaction notes

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