Hydrochloric Acid → 2,2-Bis(6-benzyloxyhexyl)ethanol

HRID 1289406Notes

Reaction equation

HRID 1289406 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:22](OCC)=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(OCC)C>[CH2:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:22][OH:23])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18920832Ethyl 2,2-bis(6-benzyloxyhexyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 189208622,2-Bis(6-benzyloxyhexyl)ethanolYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

First, 0.44 g of lithium aluminium hydride and 50 ml of diethyl ether were placed in a 100 ml flask. Then, 5.4 g of ethyl 2,2-bis(6-benzyloxyhexyl)acetate obtained in Example 2-(d) was added dropwise to the reaction mixture under ice water cooling. The reaction mixture was stirred for 1 hour at room temperature and for 1 hour under reflux. The reaction mixture was poured into cold diluted hydrochloric acid. An ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=4/1) to obtain 4.7 g of 2,2-bis(6-benzyloxyhexyl)ethanol (Y: 96%). The compound thus obtained had a purity of 97.1% by GC.

Workup

  1. temperatureunder reflux
  2. washAn ether layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-965c97fc7d054c17bad12ceeae3e9489
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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