4-Chloro-1-butanol → HCID 10442085, compound

HRID 893006Notes

Reaction equation

HRID 893006 reaction equation
C([Mg]Cl)CCC.Cl[CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[Mg].C([O:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19](=O)[CH:18]=1)C>C1COCC1>[OH:12][CH2:11][CH2:10][CH2:9][CH2:8][C:19]1[CH2:20][CH2:21][CH2:22][C:17](=[O:16])[CH:18]=1

Participants

6

Reactant 4

HCID 135694-Chloro-1-butanolHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 5462224MagnesiumHCID 178418265HCID 178418265, compound

Product 1

HCID 10442085HCID 10442085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Butylmagnesium chloride (2.0M, 20.0 ml) is added dropwise over 20 min to a solution of 4-chloro-1-butanol (4.05 g) and THF (40.0 ml). The resultant solution is stirred for 20 min and then is added dropwise over 20 min to a mixture of magnesium (1.46 g) and THF (5.0 ml). The resulting warm mixture is heated at reflux for 3 hr, and then cooled in an ice bath. A solution of 3-ethoxy-2-cyclohexene-1-one (5.39 ml) and THF (20.0 ml) is then added dropwise over 20 min. The resultant solution is allowed to warm to 20°-25° and stir for 2 hr. Acidic workup using ether and hydrochoric acid (1%) and purification by flash chromatography eluting with ethyl acetate/hexane (4/1) provides 3-(4-hydroxybutyl)-cyclohex-2-en-1-one as an oil, IR (neat) 3413, 2942, 1664, 1600, 1257, 1185 cm-1 ; MS (EI) m/e (relative %) 168 (25), 123 (25), 97 (40), 82 (36), 55 (44), 42 (100).

Workup

  1. temperatureThe resulting warm mixture
  2. temperatureis heated
  3. temperatureat reflux for 3 hr
  4. temperaturecooled in an ice bath
  5. temperatureto warm to 20°-25°
  6. customether and hydrochoric acid (1%) and purification by flash chromatography
  7. washeluting with ethyl acetate/hexane (4/1)

Sources & evidence

ORD record
ord-5b7126fa5daf41dc86f3abdb4648c1e3
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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