Hydrochloric Acid → 1-(4-Benzylthiophenyl)-2-(2-chloroethoxy)ethanol

HRID 976518Notes

Reaction equation

C([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[S:13])=[CH:10][CH:9]=1)C1C=CC=CC=1.[Cl:16][CH2:17][CH2:18][O:19][CH2:20][Mg]Cl.[Cl-].[NH4+].Cl.C([O:29][CH2:30][CH3:31])(=O)C>O1CCCC1>[CH2:12]([S:13][C:8]1[CH:15]=[CH:14][C:31]([CH:30]([OH:29])[CH2:20][O:19][CH2:18][CH2:17][Cl:16])=[CH:10][CH:9]=1)[C:11]1[CH:10]=[CH:9][CH:8]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -10 °C

Procedure

1.19 g of 4-benzylthiobenzaldehyde was dissolved in 20 ml of tetrahydrofuran. The solution was cooled to -10° C. Thereto was dropwise added 10 ml of a tetrahydrofuran solution containing 2M of 2-chloroethoxymethylmagnesium chloride in 10 minutes. The resulting mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 1 g of ammonium chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography [eluant: toluene/ethyl acetate=20/1] to obtain 1.34 g of 1-(4-benzylthiophenyl)-2-(2-chloroethoxy)ethanol.

Workup

customThe organic layer was separated
washwashed with water
dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue thus obtained
customwas purified by column chromatography [eluant: toluene/ethyl acetate=20/1]

Sources & evidence

ORD record: ord-aa05964a88e044879021ccd66d9b1f24
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612381

Reaction notes

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