4-Methylbenzoyl Chloride → N-p-toluoyl valinol

HRID 430685Notes

Reaction equation

HRID 430685 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1.[OH-].[Na+]>C(Cl)Cl>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23]([NH:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 134054-Methylbenzoyl ChlorideHCID 14798Sodium HydroxideHCID 79019ValinolHCID 81531Diisopropylethylamine

Product 1

HCID 18346087N-p-toluoyl valinolYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Diisopropylethyl amine (17.4 ml, 134 mmol) was added a solution of (DL)-valinol (9.85 g, 95 mmol) in methylene chloride (100 ml). The reaction mixture was cooled to 0 °C., treated with a solution of p-toluoyl chloride (12.8 ml, 91 mmol ) in methylene chloride (50 ml) and then allowed to warm to room temperature. After stirring for 3 hours, excess aqueous sodium hydroxide solution was added and the reaction was transferred to a separatory funnel. The organic layer was separated and the aqueous layer washed with one portion of methylene chloride. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. Chromatography eluting with 25% ethyl acetate in hexanes, followed by 50% ethyl acetate in hexanes gave N-p-toluoyl valinol (18.04 g).

Workup

  1. temperatureto warm to room temperature
  2. customthe reaction was transferred to a separatory funnel
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with one portion of methylene chloride
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. washChromatography eluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3da5c5c438e144feae7f883e23a702ff
Source dataset
uspto-grants-2001_11
Patent number
US06323223B1

Reaction notes

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