Acetate → HCID 13194923, compound

HRID 435215Notes

Reaction equation

HRID 435215 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH:13]([OH:16])[CH:14]=[CH2:15].[C:17](OC(=O)C)(=[O:19])[CH3:18].C([O-])(=O)C>N1C=CC=CC=1>[C:17]([O:16][CH:13]([C:12]#[C:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:14]=[CH2:15])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 175Acetate2×HCID 7918Acetic Anhydride2×HCID 13194922HCID 13194922, compound

Product 1

HCID 13194923HCID 13194923, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To the crude alcohol from Step (D) supra., there is added 2.34 kg. (29.6 moles) of dry pyridine. Under a blanket of nitrogen gas, 6 kg. (59.2 moles) of acetic anhydride is added at room temperature over a 6 hour period. After stirring several additional hours, a sample is pulled and analyzed on a 6' carbowax column for loss of alcohol and appearance of the desired acetate. After completion of the reaction, the crude product is transferred to a distillation apparatus where the excess acetic anhydride and residual pyridine are removed under vacuum. Finally, the product is flash distilled through a thin film evaporator, the first pass removing residual lights and unreacted 11-chloro-1-undecyne from Step (D), supra., and the second pass to flash the product off higher boiling residues at 170° C./3 mm Hg. This yields 15.3 kg. (53.8 moles) of the acetate which is sufficiently pure to carry on to the next step (yield is 55.7% based on 11-chloro-1-undecyne in Step (D) supra.).

Workup

  1. addition, there is added 2.34 kg
  2. customAfter completion of the reaction
  3. customare removed under vacuum
  4. distillationdistilled through a thin film evaporator
  5. customthe first pass removing residual lights and unreacted 11-chloro-1-undecyne from Step (D), supra
  6. customat 170° C.

Sources & evidence

ORD record
ord-1a044ebdd0fa47ae8652eee58d31cf99
Source dataset
uspto-grants-1983_08
Patent number
US04400550

Reaction notes

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