Hydrochloric Acid → HCID 53729260, compound

HRID 257858

Reaction equation

HRID 257858 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:25]=[CH:24][C:11]([S:12][C:13]2[CH:23]=[CH:22][C:16]([C:17](OCC)=[O:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.Cl>O1CCCC1>[CH3:7][C:8]1[CH:25]=[CH:24][C:11]([S:12][C:13]2[CH:23]=[CH:22][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10778595Ethyl 4-(4-methylthiophenoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 53729260HCID 53729260, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of lithium aluminum hydride (0.55 g, 14.6 mM) and dry tetrahydrofurane (100 ml) was added a solution (30 ml) of ethyl 4-(4-methylthiophenoxy)benzoate (4.00 g, 14.6 mM) in dry tetrahydrofurane at 0°-10° C., and the mixture was stirred for 12 h at room temperature. To this was added 10% HCl (200 ml) and the mixture was extracted with toluene. The extract was washed with saturated sodium hydrogen carbonate solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give 4-(4-methylthiophenoxy)benzyl alcohol (3.13 g, 87%) as colorless crystals, m.p. 103.3° C.

Workup

  1. extractionthe mixture was extracted with toluene
  2. washThe extract was washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-3220905ae74541d59b7b397439950c45
Source dataset
uspto-grants-1993_11
Patent number
US05264448

Linked notes

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