Sodium Hydroxide → HCID 86740850, compound

HRID 2119106Notes

Reaction equation

HRID 2119106 reaction equation
[CH3:1][CH:2]([C:7](=[CH:13][CH3:14])[C:8]([O:10]CC)=[O:9])[CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+]>CO.O>[CH3:1][CH:2]([C:7](=[CH:13][CH3:14])[C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86741679HCID 86741679, compound

Product 1

HCID 86740850HCID 86740850, compoundYield 98%

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 separted, acidified in 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 +0.5H2O 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. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over sodium sulphate
  6. concentrationconcentrated in vacuo to an oil which
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-b3187052cd1c4929bb84d311dbadc9ab
Source dataset
uspto-grants-1987_07
Patent number
US04681966

Reaction notes

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