Butylated Hydroxyanisole → HCID 86668285, compound

HRID 571575

Reaction equation

HRID 571575 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(=O)(OC)OC>[CH3:21][S:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 8456Butylated HydroxyanisoleHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 86668285HCID 86668285, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 12021Dimethyl CarbonateSolvent

Conditions

Temperature
25 °C

Procedure

15.0 g (83.2 mmol) of 4-hydroxy-3-tert-butylanisole and 10.5 g (104 mmol) of triethylamine were dissolved in 250 ml of dimethyl carbonate (solvent), and 11.9 g (104 mmol) of methanesulfonyl chloride was dropwise added thereto, taking 25 minutes and controlling the inner temperature at 5° C. or lower. After the addition, this was stirred at 25° C. for 1.5 hours, the reaction mixture was poured into an aqueous saturated sodium bicarbonate solution, the aqueous layer was separated, the organic layer was washed twice with water, and then the organic layer was separated and concentrated. The concentrate was purified through distillation (139° C./32 pa) to give 16.3 g of 2-tert-butyl-4-methoxyphenyl methanesulfonate (yield, 76%).

Workup

  1. customat 5° C.
  2. additionAfter the addition
  3. customthe aqueous layer was separated
  4. washthe organic layer was washed twice with water
  5. customthe organic layer was separated
  6. concentrationconcentrated
  7. distillationThe concentrate was purified through distillation (139° C./32 pa)

Sources & evidence

ORD record
ord-e6cb5f084f1e46d0a94f4f047535c050
Source dataset
uspto-grants-2015_05
Patent number
US09029024B2

Linked notes

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