Water → HCID 14787987, compound

HRID 1656652Notes

Reaction equation

HRID 1656652 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([CH2:11][CH:12](O)[CH:13]=[CH2:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O>CCOCC>[Cl:3][CH2:14]/[CH:13]=[CH:12]/[CH2:11][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 14261103HCID 14261103, compound

Product 1

HCID 14787987HCID 14787987, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (50.5 ml) was added dropwise over 1 hour to a stirred solution of 1-cyclohexyl-3-buten-2-ol (50 g) (obtained as described in European Patent Application, Publication No. 258183) in dry ether (1 litre). The solution was allowed to stand overnight and then water (750 ml) was added, and the mixture was stirred for 1 hour. The organic phase was separated, washed with water (500 ml) and saturated sodium chloride solution (2×250 ml) and dried (MgSO4). The solvent was removed by evaporation and the residual liquid distilled under high vacuum to give (2E)-1-chloro-4-cyclohexylbut-2 -ene (B), as a clear liquid (42.2 g), b.p. 64-68° C. at 0.5 mm Hg; NMR: 0.8-1.8(complex m, 11H), 2.0(t, 2H), 4.0(d, 2H), 5.5-5.9(complex m, 2H); microanalysis, found: C, 69.5; H, 10.0; Cl, 20.3%; C10H17Cl requires: C, 69.5; H, 9.9; Cl, 20.5%.

Workup

  1. customThe organic phase was separated
  2. washwashed with water (500 ml) and saturated sodium chloride solution (2×250 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. distillationthe residual liquid distilled under high vacuum

Sources & evidence

ORD record
ord-8f3eea87868043388cc5f8c2256c7eec
Source dataset
uspto-grants-1993_10
Patent number
US05254697

Reaction notes

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