Water → HCID 86675011, compound

HRID 511921Notes

Reaction equation

HRID 511921 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10].[CH:18](=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:21].O>O1CCCC1>[CH:12]1([O:11][C:9]([O:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH:18]=[O:26])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 8471TriethylamineHCID 83262Carbonochloridic acid, cyclohexyl ester

Product 1

HCID 86675011HCID 86675011, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.3 ml (45 mmol) of triethylamine and then 7.4 g (45 mmol) of cyclohexyl chloroformate are added dropwise to a solution containing 5 g (41 mmol) of salicylaldehyde in 50 ml of tetrahydrofuran at 0° C. After stirring at ambient temperature for 2 hours, the medium is treated with water and then extracted with a heptane/ethyl acetate 1/1 mixture. The organic phase is dried over magnesium sulphate, filtered and concentrated. 10.3 g of 2-(cyclohexyloxycarbonyl-oxy)benzaldehyde are obtained in the form of a yellow oil with a quantitative yield.

Workup

  1. extractionextracted with a heptane/ethyl acetate 1/1 mixture
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e13596a5e604bdca7b81739b5614b4c
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

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