Methanol → 1-Methoxy-2,2,6,6-tetramethylpiperidin-4-yl 3,5-Di-t-butyl-4-hydroxybenzoate

HRID 1590933Notes

Reaction equation

HRID 1590933 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].[OH:19][CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[N:23]([O:28][CH3:29])[C:22]([CH3:31])([CH3:30])[CH2:21]1.N1C=CC=CC=1.CO>C1(C)C=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:19][CH:20]1[CH2:25][C:24]([CH3:26])([CH3:27])[N:23]([O:28][CH3:29])[C:22]([CH3:31])([CH3:30])[CH2:21]1)=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 197683871-Methoxy-2,2,6,6-tetramethylpiperidin-4-yl 3,5-Di-t-butyl-4-hydroxybenzoateYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 7.6 g (28.3 mmol) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in toluene (35 ml) is added dropwise over 20 minutes to a solution of 5.3 g (28.3 mmol) of 4-hydroxy-1-methoxy-2,2,6,6-tetramethylpiperidine and 2.46 g (31.1 mmol) of pyridine in toluene (30 ml). The reaction temperature is kept below 60° C. during the addition and the reaction mixture is stirred for one hour at 55°-60° C. after the addition and then filtered. The filtrate is washed with 1N HCl (2×50 ml), water (100 ml), saturated NaHCO3 (100 ml), dried (magnesium sulfate), and concentrated. The crude oil is chromatographed on silica gel (9:1 hexane:ethyl acetate) to obtain 7.3 g (61% yield of a white crystalline solid, m.p. 126°-8° C. (methanol).

Workup

  1. additionThe reaction temperature is kept below 60° C. during the addition
  2. additionafter the addition
  3. filtrationfiltered
  4. washThe filtrate is washed with 1N HCl (2×50 ml), water (100 ml), saturated NaHCO3 (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe crude oil is chromatographed on silica gel (9:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-01fb11f4ad484f53b76d78d9f4107981
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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