Sulfuric Acid → HCID 20281502, compound

HRID 462882Notes

Reaction equation

HRID 462882 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:15])[CH2:9][CH2:10]C(OC)=O)=[CH:4][CH:3]=1.[CH3:16][Mg]I.S(=O)(=O)(O)O.C([O:26][CH2:27][CH3:28])C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:9][CH2:10][C:27]([OH:26])([CH3:28])[CH3:16])=[CH2:15])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 13235817HCID 13235817, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 20281502HCID 20281502, compound

Procedure

A solution of methyl 4-(4-chlorophenyl)pent-4-enoate (5.8 g, prepared as described in Example 1) in dry diethyl ether (25 ml) was added to a stirred solution of methylmagnesium iodide [from methyl iodide (8.52 g) and magnesium turnings (1.7 g)] in dry diethyl ether (50 ml) (exotherm). After 1 hour at room temperature the reaction mixture was poured into a mixture of ice and dilute sulphuric acid, then extracted with diethyl ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated under reduced pressure to give 2-(4-chlorophenyl)-5-hydroxy-5-methylhex-1-ene (5.8 g, quantitative) as a yellow oil, 1H nmr (CDCl3): δ1.22 (6H, singlet, CH3 ×2).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f684a8c429ec40ca9ef69f8e35fe8469
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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