Methanol → Tert-butyl 3-(acetyloxy)tetradecanoate

HRID 2164399Notes

Reaction equation

HRID 2164399 reaction equation
[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:22](OC(=O)C)(=[O:24])[CH3:23].CO>N1C=CC=CC=1>[C:22]([O:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic Anhydride2×HCID 14247856Tert-butyl 3-hydroxytetradecanoate

Product 1

HCID 21769584Tert-butyl 3-(acetyloxy)tetradecanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of t-butyl (3RS)-3-hydroxytetradecanoate (20.0 g) in dry pyridine (100 ml) was added acetic anhydride (7.8 ml) at ambient temperature. The mixture was stirred at the same temperature overnight. Acetic anhydride (3 ml) was added to the mixture. The mixture was stirred for additional 2 hours at the same temperature. To the mixture was added methanol (50 ml) under ice-cooling. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The organic solution was washed with 1N hydrochloric acid and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel (400 g) (chloroform:methanol 100:1 V/V) to give t-butyl (3RS)-3-acetoxytetradecanoate (14.04 g).

Workup

  1. stirringThe mixture was stirred for additional 2 hours at the same temperature
  2. temperaturecooling
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washThe organic solution was washed with 1N hydrochloric acid and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a column chromatography on silica gel (400 g) (chloroform:methanol 100:1 V/V)

Sources & evidence

ORD record
ord-f34e4618646b401ba4504237760cb756
Source dataset
uspto-grants-1985_03
Patent number
US04504472

Reaction notes

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