Hydrochloric Acid → 4-Chloro-3-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoate

HRID 845362Notes

Reaction equation

HRID 845362 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28].Cl.O>O1CCCC1.N1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([O:26][C:23]1[CH:24]=[CH:25][C:20]([Cl:19])=[C:21]([N+:27]([O-:29])=[O:28])[CH:22]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 691274-Chloro-3-nitrophenolHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 201310134-Chloro-3-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoateYield 106.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

3,5-Di-t-butyl-4-hydroxybenzoyl chloride (56.2 g; 0.209 mole) in tetrahydrofuran (70 ml) was added with stirring to a solution of 4-chloro-3-nitrophenol (36.3 g; 0.209 mole) in pyridine (170 ml) at 0° C. over 20 minutes. The reaction mixture was stirred at room temperature for 22 hours and poured into an ice cold solution of 10M-hydrochloric acid (350 ml) and water (1400 ml). The mixture was extracted into ether (500 ml) and the ethereal extract washed successively with 2M-hydrochloric acid (150 ml), 2% sodium carbonate solution (4×150 ml) and water (2×100 ml). The extract was dried and the ether removed to give a dark orange oil (90 g). This material was chromatographed (silica) eluting with 4:1 hexane:ethyl acetate, to give the product (60.6 g; 72%) as a yellow viscous oil.

Workup

  1. extractionThe mixture was extracted into ether (500 ml)
  2. extractionthe ethereal extract
  3. washwashed successively with 2M-hydrochloric acid (150 ml), 2% sodium carbonate solution (4×150 ml) and water (2×100 ml)
  4. customThe extract was dried
  5. customthe ether removed

Sources & evidence

ORD record
ord-c18970561e68411fa971b2b9c6f34339
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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