p-Toluenesulfonic acid → HCID 23341279, compound

HRID 971943Notes

Reaction equation

HRID 971943 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-2ac44a37a44442f4a29c46c316855401
Source dataset
uspto-grants-1979_07
Patent number
US04162154

Reaction notes

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