Hydrochloric Acid → HCID 69946045, compound

HRID 1166875Notes

Reaction equation

HRID 1166875 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[S:10]1[CH:14]=[CH:13]C(C=O)=[CH:11]1.Cl.[CH3:18][CH2:19][O:20]CC>>[S:10]1[CH:14]=[CH:13][C:1]([C:2]2([CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]2)[CH2:18][CH2:19][OH:20])=[CH:11]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 7498Benzyl BromideHCID 681353-ThiophenecarboxaldehydeHCID 5462224Magnesium

Product 1

HCID 69946045HCID 69946045, compoundYield 78%

Conditions

Temperature
-10 °C

Procedure

Benzyl bromide (25.65 g, 150 mmol) was added dropwise over 8 h to a suspension of magnesium (3.6 g, 150 mmol) in ether (75 ml) dissolved in ether (30 ml). The resulting mixture was cooled to −10° C. 3-thiophenecarboxaldehyde in ether (45 ml) over 30 min was then added and the resultant reaction mixture was stirred at room temperature for 6 h. This was cooled to 0° C. and the reaction mixture was decomposed by addition of 0.1 N HCl. The ether layer was separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic layers was dried over MgSO4 and filtered. Removal of the solvent gave 1-(3-thienyl)phenethyl alcohol (16 g, 78% yield).

Workup

  1. customthe resultant reaction mixture
  2. temperatureThis was cooled to 0° C.
  3. customThe ether layer was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialThe combined organic layers was dried over MgSO4
  6. filtrationfiltered
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-bd4575523fde48b6b6b24b6f75061209
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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