Sodium Hydroxide → HCID 86740850, compound

HRID 1982191Notes

Reaction equation

HRID 1982191 reaction equation
[CH2:1]([C:3](C)=[C:4]([CH:8]([CH2:10][CH2:11][CH2:12][CH3:13])[CH3:9])[C:5]([O-:7])=[O:6])C.[OH-].[Na+]>CO.O>[CH3:9][CH:8]([C:4](=[CH:3][CH3:1])[C:5]([OH:7])=[O:6])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86740851HCID 86740851, compound

Product 1

HCID 86740850HCID 86740850, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl(2-hexyl)but-2-enoate (12 g, 0.06M) in methanol (150 ml) was treated with sodium hydroxide (15 g, 0.375M) in water (100 ml) under reflux for 6 hours. The solvents were then removed in vacuo and the residue taken up in water and extracted with dichloromethane. The aqueous phase was separated, acidified to pH1 with concentrated hydrochloric acid and extracted with dichloromethane. The extract was dried over sodium sulphate and concentrated in vacuo to an oil which was distilled in vacuo to afford E and Z (2-hexyl)but-2-enoic acid (10.1 g, 0.06M) as the main fraction (b.p. 100°-110° C. at 0.5 mm Hg) (Found: C, 68.2; H, 10.4. C10H18O2 +0.5 H2O requires: C,68.5; H, 9.7%); δ(CDCl3) 0.88 (3H, m, CH3); 1.3 (8H, m, (CH2)4); 1.84 and 2.04 (3H, each m, each CH3CH); 2.32 (2H, t, J=8 Hz, CH2) 6.14 and 6.94 (1H, each q, each J=8 Hz, CH).

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe solvents were then removed in vacuo
  3. extractionextracted with dichloromethane
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over sodium sulphate
  7. concentrationconcentrated in vacuo to an oil which
  8. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-ca71781befa74ef39b2314efd06a1f01
Source dataset
uspto-grants-1986_06
Patent number
US04595700

Reaction notes

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