p-Toluenesulfonic acid → HCID 21036273, compound

HRID 1789646Notes

Reaction equation

HRID 1789646 reaction equation
[C:1]([C:9]1[C:10]([OH:22])=[C:11]([C:16]([CH3:21])=[CH:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:13][C:14]=1[OH:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24](=[CH:26][CH2:27][CH2:28][CH:29]([CH2:31][CH2:32]O)[CH3:30])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1CCCCC1>[CH3:30][CH:29]([CH2:28][CH2:27][CH2:26][C:24]([CH3:25])=[CH2:23])[CH2:31][CH2:32][O:19][C:18](=[O:20])/[CH:17]=[C:16](/[C:11]1[CH:12]=[CH:13][C:14]([OH:15])=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]=1[OH:22])\[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8842CitronellolHCID 69625726HCID 69625726, compound

Product 1

HCID 21036273HCID 21036273, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of 3-(3-benzoyl-2,4-dihydroxyphenyl)-but-2-enoic acid (5.97 g, 20.0 mmol), citronellol (3.13 g, 20.0 mmol) and p-toluenesulfonic acid (1 g) in cyclohexane (150 mL) is refluxed for 6 h under vacuum using a Dean Stark separator. The reaction mixture is partitioned between methylene chloride (150 mL) and water (150 mL); the organic layer is removed and washed with methylene chloride (100 mL). The combined organic layers are washed sequentially with saturated sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated to give (E)-3-(3-benzoyl-2,4-dihydroxyphenyl)-but-2-enoic acid 3,7-dimethyl-oct-7-enyl ester as an oil which can be purified by flash chromatography.

Workup

  1. customThe reaction mixture is partitioned between methylene chloride (150 mL) and water (150 mL)
  2. customthe organic layer is removed
  3. washwashed with methylene chloride (100 mL)
  4. washThe combined organic layers are washed sequentially with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e27fdbc38b8b4db2b1d2d58530a7c696
Source dataset
uspto-grants-2006_07
Patent number
US07071151B2

Reaction notes

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