Benzyl Alcohol → HCID 12889632, compound

HRID 1680921Notes

Reaction equation

HRID 1680921 reaction equation
[C:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:11][C:7]=1[C:8](Cl)=[O:9])(=[O:4])[CH2:2][CH3:3].[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:11][C:7]=1[C:8]([O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:9])(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 1049PyridineHCID 23455043HCID 23455043, compound

Product 1

HCID 12889632HCID 12889632, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
26 °C

Procedure

To a solution of 2,5-dipropionoxybenzoyl chloride (10.3 gr., 0.036 mole) in 30 ml dry chloroform at 0° C. is added dropwise over a six hour period a solution of benzyl alcohol (3.45 gr., 0.032 mole) and pyridine (5.05 gr., 0.064 mole) in 6 ml of dry chloroform. The temperature is maintained at 0° C.-5° C. during the addition and the entire operation is performed under an argon atmosphere. The reaction is stirred at 26° C. for 16 hours and poured into 50 ml of cold water. The organic portion is extracted with 450 ml of ether and the organic layer is washed with 80 ml of 15% HCL (hydrochloric acid), 3×100 ml water, 100 ml of 1 N sodium hydroxide, 3×100 ml water, and dried over magnesium sulfate. Evaporation of the solvents affords 10.22 grams (90%) of benzyl 2,5-dipropionoxybenzoate as a colorless liquid. Distillation in a Hickman still affords 7.0 grams (60%) of benzyl 2,5-dipropionoxybenzoate as a colorless liquid of b.p. 227° C./0.14 mm.

Workup

  1. temperatureThe temperature is maintained at 0° C.-5° C. during the addition
  2. extractionThe organic portion is extracted with 450 ml of ether
  3. washthe organic layer is washed with 80 ml of 15% HCL (hydrochloric acid), 3×100 ml water, 100 ml of 1 N sodium hydroxide, 3×100 ml water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-8a88a1ffad1f498db65249549dbb389b
Source dataset
uspto-grants-1981_06
Patent number
US04276430

Reaction notes

Loading…