Hydrochloric Acid → Carbonic acid tert-butyl ester 2-formyl-phenyl ester

HRID 511916Notes

Reaction equation

HRID 511916 reaction equation
C(N(CC)C(C)C)(C)C.C(O[C:15]([O:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)(C)(C)C.C(=O)[C:26]1[C:27](=[CH:29][CH:30]=[CH:31][CH:32]=1)[OH:28].Cl>O1CCCC1>[C:21]([O:20][C:18]([O:17][C:15]1[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=1[CH:27]=[O:28])=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 17748171Carbonic acid tert-butyl ester 2-formyl-phenyl esterYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

350 mg (2.8 mmol) of N,N-dimethylaminopyridine and 8.1 ml (46.9 mmol) of N,N-diisopropylethylamine are added to a solution containing 20.9 g (95.7 mmol) of di(tert-butyl)dicarbonate in 150 ml of tetrahydrofuran under a stream of nitrogen. 10 ml (93.8 mmol) of salicylaldehyde are added dropwise. After stirring at ambient temperature for 2 hours, the medium is treated with a 1N aqueous hydrochloric acid solution and then extracted with a heptane/ethyl acetate 1/1 mixture. The organic phase is dried over magnesium sulphate, filtered and concentrated. 21.5 g of 2-(tert-butoxycarbonyloxy)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-598539de29a94b51b4fac1b19569c04f
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

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