4-tert-Butylbenzoic acid → Methyl 4-[2-(4-tert-butylbenzamido)ethoxy]benzoate

HRID 1762174Notes

Reaction equation

HRID 1762174 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:27][CH2:28][CH2:29][O:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[O:11])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 74034-tert-Butylbenzoic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Product 1

HCID 14426625Methyl 4-[2-(4-tert-butylbenzamido)ethoxy]benzoateYield 91.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

p-tert-Butylbenzoic acid (5.35 g) and 3.34 g of triethylamine were dissolved in 70 ml of chloroform and 3.26 g of ethyl chloroformate was dropped into the above mixture with stirring and cooling at 0° to 5° C. After the dropping, the mixture was stirred at the same temperature for 30 minutes and, after addition of 5.86 g of methyl 4-(2-aminoethoxy)benzoate thereto, the mixture was stirred for 6 hours more. The reaction solution was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and water, dried with anhydrous magnesium sulpahte, concentrated in vacuo, and the residue was crystallised with n-hexane to give 9.8 g of crystals which were further recrystallised from ethyl acetate to give 7.64 g (yield: 71.65%) of the product, m.p. 112°-114° C.

Workup

  1. temperaturecooling at 0° to 5° C
  2. stirringAfter the dropping, the mixture was stirred at the same temperature for 30 minutes
  3. stirringthe mixture was stirred for 6 hours more
  4. washThe reaction solution was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and water
  5. dry with materialdried with anhydrous magnesium sulpahte
  6. concentrationconcentrated in vacuo
  7. customthe residue was crystallised with n-hexane

Sources & evidence

ORD record
ord-7c50a48fc6d84b4197668e9e297aa4e0
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

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