Hydrochloric Acid → Benzenesulfinic acid, 4-methyl-, methyl ester

HRID 844529Notes

Reaction equation

HRID 844529 reaction equation
[CH3:1]O.Cl.C1(C)C([S:10]([OH:12])=[O:11])=CC=CC=1.[Na].O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:1][O:12][S:10]([C:19]1[CH:20]=[CH:21][C:16]([CH3:22])=[CH:17][CH:18]=1)=[O:11]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 887Methanol2×HCID 962WaterHCID 1140TolueneHCID 67085813HCID 67085813, compound

Product 1

HCID 10285823Benzenesulfinic acid, 4-methyl-, methyl ester

Conditions

Temperature
22.5 °C

Procedure

To a 5-liter, 3-neck round bottom flask, was added 2845 mls of methanol (5 volumes) and was bubbled in 165.58 grams (1.4 equivalents, 4.47 gmoles) of anhydrous HCl. Heat evolved during addition of HCl to MeOH. The flask was maintained at a temperature range from 20 to 25° C. by cooling and adjusting addition rate. Sodium toluene sulfinic acid (1.0 equivalents, 569 grams, 3.19 gmoles) was added and stired at room temperature for 1 to 4 hours. Water 2850 mls (5 volumes) was added, then and 2850 mls of toluene (5 volumes.) The mixture was stirred from 1 to 30 minutes and the layers were allowed to separate The layers were separated and the aqueous layer was back extracted twice using 1425 mls (2.5 volumes) of toluene for each back extraction. All toluene layers were combined and washed two times with 1425 mls (2.5 volumes) of 1 molar sodium bicarbonate solution for each wash. The layers were separated and the toluene layerers was concentrated under vacuum to approximately 3 volumes. The volumes were concentrated to a small alloquote to an oil on rotovap indicated a final weight yield of 476.78 grams of ester, 87.7% of theory weight.

Workup

  1. temperatureHeat
  2. temperatureby cooling
  3. additionaddition rate
  4. customto separate The layers
  5. customwere separated
  6. extractionthe aqueous layer was back extracted twice
  7. extractionfor each back extraction
  8. washwashed two times with 1425 mls (2.5 volumes) of 1 molar sodium bicarbonate solution for each wash
  9. customThe layers were separated
  10. concentrationthe toluene layerers was concentrated under vacuum to approximately 3 volumes
  11. concentrationThe volumes were concentrated to a small alloquote to an oil on rotovap

Sources & evidence

ORD record
ord-00aedbcc1f3044e09462564a582a9fd1
Source dataset
uspto-grants-2002_04
Patent number
US06380397B1

Reaction notes

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