p-Toluenesulfonic acid → HCID 20194899, compound

HRID 653511Notes

Reaction equation

HRID 653511 reaction equation
[CH3:1][O:2][C:3]([C:5]([C:15]([O:17][CH3:18])=[O:16])([CH2:8][CH2:9][CH:10]([O:13][CH3:14])[O:11]C)[CH2:6]O)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:14][O:13][CH:10]1[O:11][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([C:15]([O:17][CH3:18])=[O:16])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 20194908HCID 20194908, compound

Product 1

HCID 20194899HCID 20194899, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of dimethyl-1-hydroxy-5,5-dimethoxypentane-2,2-dicarboxylate made in accordance with Example I (8.4 g, 0.032 mol), p-toluenesulfonic acid (0.052 g, 0.027 mmol) in dry benzene (600 ml) was allowed to reflux through a Soxhlet extractor for 2 hours. The Soxhlet thimble was charged with Type 4 A molecular sieves (ca 20 g). After the mixture was cooled to room temperature, anhydrous potassium carbonate (7 g, 0.05 mol) was added, and the mixture was stirred for 30 min. The mixture was filtered and the solvent was removed by a rotary evaporator. The residual amber oil was distilled under reduced pressure. Yield of the product, which had a bp of 95°-100° C. (1 mmHg), was 84%.

Workup

  1. temperatureto reflux through a Soxhlet extractor for 2 hours
  2. additionThe Soxhlet thimble was charged with Type 4 A molecular sieves (ca 20 g)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed by a rotary evaporator
  5. distillationThe residual amber oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-459bfeaff7dc4019ad42865d378cc1c8
Source dataset
uspto-grants-1987_06
Patent number
US04677190

Reaction notes

Loading…