Hydrochloric Acid → (4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester

HRID 2057330Notes

Reaction equation

HRID 2057330 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH:12]1[CH2:17][CH2:16][C:15](=[CH:18][O:19]C)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69194804(4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester

Product 1

HCID 86584993(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 495 g (1710.6 mmol) of (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.7 l THF was treated with 3.42 l of aqueous 1N HCl at RT and heated at reflux for 2 h. The reaction was cooled to RT and extracted with TBME (1.7 and 0.9 l). The organic phase was washed with aqueous 1M NaHCO3, dried (Na2SO4), filtered and evaporated to give 457.4 (97%) of crude (4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester (trans:cis ca 70:30).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. extractionextracted with TBME (1.7 and 0.9 l)
  4. washThe organic phase was washed with aqueous 1M NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-26a7a23953a5448f95b35cf996428487
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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