Hydrogen Peroxide → Tert.-Butyl 22-Hydroxydocosanoate

HRID 2399984Notes

Reaction equation

HRID 2399984 reaction equation
[C:1]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[CH:22].[OH2:29].[OH-].[Na+].OO>C1COCC1.C(OCC)(=O)C>[OH:29][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 86749000Docos-21-ynoic Acid. Tert.-Butyl Ester

Product 1

HCID 19385096Tert.-Butyl 22-HydroxydocosanoateYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the acetylene (33) (0.4 g, 1.02 mmol) in dry THF (5 ml) at room temperature under nitrogen was treated with borane-dimethyl sulphide complex (1.04 ml of a 2M solution in THF, 2.08 mmol) and the resulting solution stirred for 1 hour, after which time no starting material was present on tlc. The reaction was then treated sequentially with water (2 ml), 2N aqueous sodium hydroxide (1 ml) and 30% hydrogen peroxide (1 ml). The resulting solution was left a further 15 minutes, then ethyl acetate added and the organic layer separated. The aqueous layer was re-extracted with ethyl acetate, the organic layers combined, dried (MgSO4) and evaporated. The crude product obtained in this manner was purified on silica (5 g). Elution with 10% ethyl acetate in petrol gave tert.-butyl 22-hydroxydocosanoate (34) as a white solid (0.23 g, 54%).

Workup

  1. waitThe resulting solution was left a further 15 minutes
  2. customthe organic layer separated
  3. extractionThe aqueous layer was re-extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product obtained in this manner
  7. customwas purified on silica (5 g)
  8. washElution with 10% ethyl acetate in petrol

Sources & evidence

ORD record
ord-1eec539b14ba4a17a555f3b1e237ff30
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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