Citric Acid → 2-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol

HRID 2223910Notes

Reaction equation

HRID 2223910 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:35]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:38]([O:37][CH2:36][C:34]1[CH:35]=[C:30]([O:29][CH2:28][CH2:27][C:21]2([CH2:20][CH2:19][OH:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:31]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:33]=1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11078149TBAF tetrahydrofuranHCID 691465871-[2-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene

Product 1

HCID 597148422-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanolYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene (1.13 g) dissolved in tetrahydrofuran (7 mL) was added a 1M tetrabutylammonium fluoride/tetrahydrofuran solution (2.8 mL) dropwise at room temperature. The solution was stirred for 15 hours. A 10% aqueous citric acid solution was added to the solution, and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)] to give the title compound (439 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-d06f058558e0464c92bac6474ccdea20
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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