Acetic Anhydride → HCID 15321954, compound

HRID 926209Notes

Reaction equation

HRID 926209 reaction equation
[CH3:1][C:2]([OH:8])([CH2:4][CH2:5][CH2:6][CH3:7])[CH3:3].[C:9](OC(=O)C)(=[O:11])[CH3:10].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:9]([O:8][C:2]([CH3:3])([CH2:4][CH2:5][CH2:6][CH3:7])[CH3:1])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 122402-Methylhexan-2-olHCID 516892Sodium Bicarbonate

Product 1

HCID 15321954HCID 15321954, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

2-Methylhexan-2-ol (30.0 g, 0.258 mol) was treated with acetic anhydride (36.6 mL, 0.387 mol). Pyridine (30.0 mL, excess) was added dropwise over a 3 min period at 23° C. Then 4-(N,N-dimethylamino)-pyridine (1.27 g, 10.0 mmol) was added. The reaction was heated to 70° C. for 16 h. The reaction was cooled to 23° C. and poured onto 300 mL of crushed ice. After 15 min of stirring, most of the ice had melted. Solid NaHCO3 was added in portions (bubbling) until the pH was 9. The system was extracted with two portions of diethyl ether (100 mL, then 50 mL). The combined extracts were washed with 1.0 M aq. CuSO4 monohydrate (4×50 mL), dried over MgSO4, and filtered. The filtrate was distilled at ambient pressure at a bath temperature of 80-100° C. to remove most of the diethyl ether. The resulting oil left in the pot was fractionally distilled through a Snyder column with 3 chambers under reduced pressure (6-8 mmHg). A small-volume forerun was collected and discarded (bp<45° C.). The main fraction contained 2-methylhexan-2-yl acetate (bp 45-48° C.). 1H NMR (400 MHz, CDCl3) δ 1.94 (s, 3H), 1.74-1.68 (m, 2H), 1.40 (s, 6H), 1.33-1.22 (m, 4H), 0.88 (t, J=6.8 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to 23° C.
  2. extractionThe system was extracted with two portions of diethyl ether (100 mL
  3. washThe combined extracts were washed with 1.0 M aq. CuSO4 monohydrate (4×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. distillationThe filtrate was distilled at ambient pressure at a bath temperature of 80-100° C.
  7. customto remove most of the diethyl ether
  8. waitThe resulting oil left in the
  9. distillationpot was fractionally distilled through a Snyder column with 3 chambers under reduced pressure (6-8 mmHg)
  10. customA small-volume forerun was collected

Sources & evidence

ORD record
ord-69918c2adb224ca6873051e398938491
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…