Acetic Acid → HCID 10517494, compound

HRID 1584523Notes

Reaction equation

HRID 1584523 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[O:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O)(=O)C.Cl>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:19]2[CH2:20][CH2:21][O:16][CH2:17][CH:18]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 73112,4-Di-tert-butylphenolHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 10517494HCID 10517494, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 21.9 g (0.106 mol) of 2,4-di-tert-butylphenol, 5.3 g (0.053 mol) of tetrahydro-4H-pyran-4-one and 5 ml of acetic acid is melted melted together and is then saturated, with stirring, with hydrochloric acid gas at 40-45° C. After standing for 60 hours at room temperature, the reaction mixture is diluted with toluene and washed with water, sodium chloride solution and sodium hydrogencarbonate solution. The organic phase is dried over magnesium sulfate and concentrated on a rotary evaporator. The residue is crystallised from methanol, giving 7.2 g (47%) of 2,4-di-tert-butyl-6-(3,6-dihydro-2H-pyran-4-yl)phenol, m.p. 135-139° C. (compound (103), Table 1).

Workup

  1. washwashed with water, sodium chloride solution and sodium hydrogencarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue is crystallised from methanol

Sources & evidence

ORD record
ord-50faab5277ee4a47b8561e5d79218f1f
Source dataset
uspto-grants-1999_08
Patent number
US05932642

Reaction notes

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