Water → Methyl 2-hydroxy-4-octadecenoate

HRID 1031038Notes

Reaction equation

HRID 1031038 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[O:3].[CH2:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C.O>ClCCl>[OH:3][CH:2]([CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:1]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123951-HexadeceneHCID 70205Acetic acid, 2-oxo-, methyl ester

Product 1

HCID 54429174Methyl 2-hydroxy-4-octadecenoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl glyoxalate (8.80 g, 0.1 mol, 1.0 eq) and 1-hexadecene (44.80 g, 0.2 mol, 2.0 eq) are dissolved in dry dichloromethane (200 ml, freshly distilled from calcium hydride) under a nitrogen atmosphere. Stannic chloride (3.51 ml, 0.03 mol, 0.3 eq) is added dropwise with stirring and cooling at 0° C. (ice/water bath). After half an hour the reaction mixture is allowed to warm to room temperature and stirred for a further 21 hours before being neutralised with triethylamine (4.2 ml, 0.03 mol, 0.3 eq) with a further 5 minutes stirring. Water (50 ml) and dichloromethane (100 ml) are added, the organic layer is separated, washed in turn with water (50 ml) and brine (50 ml), dried over anhydrous magnesium sulphate and evaporated. The crude oil is purified by short path distillation (bp 220-230° C./0.7 mm Hq) to furnish the ester product as a colourless liquid.

Workup

  1. distillationfreshly distilled from calcium hydride) under a nitrogen atmosphere
  2. waitAfter half an hour the reaction mixture is allowed
  3. stirringstirred for a further 21 hours
  4. stirringstirring
  5. customthe organic layer is separated
  6. washwashed in turn with water (50 ml) and brine (50 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. distillationThe crude oil is purified by short path distillation (bp 220-230° C./0.7 mm Hq)

Sources & evidence

ORD record
ord-fb3b67089e874b65acc3b6fe0b7d9975
Source dataset
uspto-grants-1992_04
Patent number
US05108751

Reaction notes

Loading…