p-Toluenesulfonic acid → 2-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decan

HRID 342036Notes

Reaction equation

HRID 342036 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:12][CH2:13][CH:14]([OH:17])[CH2:15]O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]2([O:17][CH:14]([CH2:13][Cl:12])[CH2:15][O:11]2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 72903-Chloro-1,2-propanediolHCID 73924-tert-Butylcyclohexanone

Product 1

HCID 143262942-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decanYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

97.0 g (0.597 mol) of 4-t-butylcyclohexanone and 134.7 g (1.184 mol) of 3-chloro-1,2-propanediol are dissolved in 1100 ml of toluene in the presence of 11.5 g (0.060 mol) of PTSA. The mixture is brought to reflux for 6 hours while removing the water formed using a Dean-Stark trap. The reaction mixture is brought to room temperature and washed twice with 1500 ml of an aqueous solution containing 5% of NaHCO3. The organic phase is dried over MgSO4 and concentrated under vacuum. The residual oil is used directly in the following step (yield: 99%; NMR analysis)

Workup

  1. temperatureto reflux for 6 hours
  2. customwhile removing the water
  3. customformed
  4. customis brought to room temperature
  5. washwashed twice with 1500 ml of an aqueous solution
  6. additioncontaining 5% of NaHCO3
  7. dry with materialThe organic phase is dried over MgSO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1ee9b5c4fd884bdaa1584a4a4cb92054
Source dataset
uspto-grants-1999_01
Patent number
US05856514

Reaction notes

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