(E)-2-buten-1-ol mesylate → 1-chloro-(Z,E)-7,10-dodecadiene

HRID 2073670Notes

Reaction equation

HRID 2073670 reaction equation
S(OC/C=C/C)(=O)(=O)C.[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[C:18][CH2:19]/[CH:20]=[CH:21]/[CH3:22]>>[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]/[CH3:22]

Participants

3

Reactant 2

HCID 13541297(E)-2-buten-1-ol mesylateHCID 146237351-chloro-(E)-10-dodecen-7-yne

Product 1

HCID 146237371-chloro-(Z,E)-7,10-dodecadieneYield 93%

Procedure

The synthetic procedure was about the same as in Example 1 excepting replacement of 271.5 g of (E)-2-butenyl chloride with 450 g (3 moles) of (E)-2-buten-1-ol mesylate which were added dropwise to the reaction mixture kept at 30° C. or below followed by further continued agitation of the reaction mixture at 30° C. for 1.5 hours to effect hydrolysis so that 216 g of 1-chloro-(E)-10-dodecen-7-yne were obtained in a purity of 94%. The yield was 35% of the theoretical value. Partial hydrogenation of this ene-yne compound in the same manner as in Example 1 gave 203 g of 1-chloro-(Z,E)-7,10-dodecadiene in a purity of 88%. The yield was 88% of the theoretical value.

Workup

  1. additionwere added dropwise to the reaction mixture
  2. customkept at 30° C. or below
  3. customwere obtained in a purity of 94%

Sources & evidence

ORD record
ord-46a3bec953b8437d816f2155d0d613b7
Source dataset
uspto-grants-1990_04
Patent number
US04918252

Reaction notes

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