Water → HCID 58234690, compound

HRID 511919Notes

Reaction equation

HRID 511919 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].[CH:15](=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18].O>C1(C)C=CC=CC=1.O1CCCC1>[CH:12]([O:11][C:9]([O:18][C:17]1[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=1[CH:15]=[O:23])=[O:10])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 7917Isopropyl chloroformateHCID 8471Triethylamine

Product 1

HCID 58234690HCID 58234690, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

26 ml (190 mmol) of triethylamine and then 185 ml (190 mmol) of a 1M solution of isopropyl chloroformate in toluene are added dropwise to a solution containing 15 g (120 mmol) of salicylaldehyde in 150 ml of tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for 2 hours and then at ambient temperature for 18 hours. Water is added and the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated. 27 g of 2-(isopropoxy-carbonyloxy)benzaldehyde are obtained in the form of a yellow oil with a quantitative yield.

Workup

  1. waitat ambient temperature for 18 hours
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-14839e97148948acbb50cc02e5969a07
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

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