Benzyl Alcohol → HCID 67375539, compound

HRID 1027345Notes

Reaction equation

HRID 1027345 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH3:13][O:14][CH:15]([O:19]C)[CH2:16][C:17]#[N:18].C(O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC=CC=1>C(N(CC)CC)C>[CH2:12]([O:19][CH:15]([O:14][CH2:13][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][C:17]#[N:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 937313,3-DimethoxypropiononitrileHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 67375539HCID 67375539, compoundYield 871.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

4.95 g of p-toluenesulfonic acid monohydrate was added to 30.0 g of 3,3-dimethoxypropionitrile, 67.63 g of benzyl alcohol and 100 ml of toluene, and the mixture was stirred at 110° C. for 8 hours. The reaction solution was returned to room temperature, and 5.26 g of triethylamine was added. After stirring for 5 minutes, the reaction solution was transferred to a separating funnel and washed with 200 ml of an aqueous 1 mass % potassium carbonate solution once and then with 200 ml of distilled solution three times. Toluene and the unreacted raw materials were removed by distillation under reduced pressure to obtain 60.6 g of 3,3-dibenzyloxypropionitrile. Thereto, 21.36 g of acetyl chloride was added, and the mixture was stirred at 45° C. for 6 hours. The reaction solution was returned to room temperature, and unreacted acetyl chloride was removed by distillation under reduced pressure. The reaction solution was analyzed by 1H-NMR, as a result, the concentration of 3-chloro-3-benzyloxypropionitrile in the reaction solution was 54.2 mass %.

Workup

  1. customwas returned to room temperature
  2. stirringAfter stirring for 5 minutes
  3. customthe reaction solution was transferred to a separating funnel
  4. washwashed with 200 ml of an aqueous 1 mass % potassium carbonate solution once
  5. customToluene and the unreacted raw materials were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-42ac9e871fc84998874e6f2d77380ccd
Source dataset
uspto-grants-2014_05
Patent number
US08735048B2

Reaction notes

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