Ammonium Chloride → 2-Benzoyloxymethyl-4-hydroxymethylbenzyl benzoate

HRID 584290Notes

Reaction equation

HRID 584290 reaction equation
[C:1]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:13][C:12]=1[CH2:26][O:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C(OCC)(=O)C>[C:1]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=1[CH2:26][O:27][C:28](=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 697935022-Benzoyloxymethyl-4-(tert-butyldimethylsilanyloxymethyl)benzyl benzoate

Product 1

HCID 697922262-Benzoyloxymethyl-4-hydroxymethylbenzyl benzoateYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

69 g (140 mmol) of 2-benzoyloxymethyl-4-(tert-butyldimethylsilanyloxymethyl)benzyl benzoate are placed in 450 ml of ethyl acetate in a round-bottomed flask and under a stream of nitrogen. 178 ml of tetrabutylammonium fluoride (1M/THF) are added. The medium is stirred for 30 minutes at room temperature. It is then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (40/60) to give 46.6 g (88%) of the expected product in the form of a white powder with a melting point of 92° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluted with a mixture of heptane and ethyl acetate (40/60)

Sources & evidence

ORD record
ord-50c318bd534c4327a3ed0a4616720d6c
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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