Hydrochloric Acid → HCID 19920496, compound

HRID 1648533Notes

Reaction equation

HRID 1648533 reaction equation
[C:1](=[O:12])([O:7][CH2:8][CH2:9][CH2:10][CH3:11])OCCCC.C[O-:14].[K+].[C:16]([C:20]1[CH:25]=[CH:24][C:23](C)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C([CH:31]1CC[C:34](=[O:37])[CH2:33][CH2:32]1)(C)(C)C.Cl>C(O)CCC>[C:16]([CH:20]([CH2:21][CH2:22][C:1]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:12])[CH2:25][CH2:24][C:23]([O:37][CH2:34][CH2:33][CH2:32][CH3:31])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73904-tert-ButyltolueneHCID 73924-tert-ButylcyclohexanoneHCID 68333Dibutyl carbonateHCID 23664618Potassium methoxide

Product 1

HCID 19920496HCID 19920496, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

348 g (2 mol) of di-n-butyl carbonate and 140 g (2 mol) of potassium methoxide powder were placed together with 500 ml of 4-tert-butyltoluene in a reaction vessel equipped with a stirrer. 154 g (1 mol) of 4-tert-butylcyclohexanone were metered in at 40° C. over the course of 4 h. The mixture was subsequently stirred with 400 g of n-butanol at 110° C. for 3 h. 600 ml of 10% strength HCl were then added, forming two phases which were easily separated. The aqueous phase was extracted several times with 4-tert-butyl toluene. The combined organic phases were distilled to give 180 g of dibutyl 4-tert-butylpimelate, corresponding to a yield of 74%,

Workup

  1. customequipped with a stirrer
  2. customwere metered in at 40° C. over the course of 4 h
  3. customforming two phases which
  4. customwere easily separated
  5. extractionThe aqueous phase was extracted several times with 4-tert-butyl toluene
  6. distillationThe combined organic phases were distilled

Sources & evidence

ORD record
ord-f01842b4d262428bb7627679624c1184
Source dataset
uspto-grants-1995_07
Patent number
US05436365

Reaction notes

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