Benzene → HCID 21509253, compound

HRID 1287522Notes

Reaction equation

HRID 1287522 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11](O)[CH2:12][CH3:13].C1C=CC=CC=1.S(=O)(=O)(O)O>O>[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:11][CH2:12][CH3:13])=[O:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10311-PropanolHCID 1118Sulfuric AcidHCID 54432-Mercaptobenzoic Acid

Product 1

HCID 21509253HCID 21509253, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g (0.32 mole) of 2-mercaptobenzoic acid, 30 g (0.5 mole) of n-propanol, 200 ml of benzene and 1.0 g of sulfuric acid (93%) was stirred at reflux in a flask equipped with a condenser and Dean-Stark water separator. After 24 hours at reflux, 6.0 ml of water was collected in the water separator. The mixture was cooled to ambient temperature, washed with 150 ml of 10% sodium carbonate solution, washed with three 150 ml water washes, dried over sodium sulfate, filtered and concentrated using a rotary evaporator. The residual oil was distilled to give n-propyl 2-mercaptobenzoate: 41.5 g (62% yield); bp 103°C/0.5 mm; mol wt 196:

Workup

  1. temperatureat reflux in a flask
  2. customequipped with a condenser
  3. temperatureAfter 24 hours at reflux
  4. custom6.0 ml of water was collected in the water separator
  5. washwashed with 150 ml of 10% sodium carbonate solution
  6. washwashed with three 150 ml water washes
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customa rotary evaporator
  11. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-ef0fa31aa04043e7b2f8b00cd1f8a1e2
Source dataset
uspto-grants-1976_10
Patent number
US03984573

Reaction notes

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