p-Toluenesulfonic acid → HCID 23341279, compound

HRID 27636Notes

Reaction equation

HRID 27636 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:7]=1)(=[O:4])=[O:3].CO[C:20](OC)([CH3:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][C:20]([CH3:22])([CH3:21])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:8]=2[CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane2×HCID 233412804-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate

Product 1

HCID 23341279HCID 23341279, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methylsulphonate (10 parts) (from Example 1), 2,2-dimethoxypropane (17 parts) and p-toluenesulphonic acid (0.1 parts) was heated in toluene (90 parts) with distillation of low boiling fraction and slow addition of further 2,2-dimethoxypropane (17 parts) for 1 hour. The resulting solution was cooled, washed with aqueous sodium hydroxide solution and with water, dried over magnesium sulphate and the solvent evaporated off under reduced pressure. The crude product was distilled yielding 9 parts of 4,5-dihydro-2,2,5,5-tetramethyl-1,3-benzodioxepin-7-yl methanesulphonate, boiling point 130°-142° C./0.2 mm Hg. Recrystallisation from aqueous ethanol gave the pure product (4.8 parts), melting point 65°-67° C.

Workup

  1. temperatureThe resulting solution was cooled
  2. washwashed with aqueous sodium hydroxide solution and with water
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent evaporated off under reduced pressure
  5. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-b7c85b67ac23473d88d0d1ddc3a8592a
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Reaction notes

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