M-Cresol → Benzoic acid, 3-methylphenyl ester

HRID 1975822Notes

Reaction equation

HRID 1975822 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].C(N(CC)CC)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:16]([O:7][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:8])[CH:1]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 69193Benzoic acid, 3-methylphenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0°-5° C.) solution of 5.0 g (0.046 mol) of m-cresol in 20 mL of methylene chloride containing 5.16 g (0.051 mol) of triethylamine was added dropwise a solution containing 6.47 g (0.046 mol) of benzoyl chloride in 20 mL of methylene chloride. A precipitate formed upon addition. The reaction mixture was stirred several hours at room temperature and was then filtered. The filtrate was washed with water (25 mL) and then with brine (25 mL). The organic phase was removed and dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The crude product amounted to 9.66 g. An analytical sample (m.p. 51°-54° C.) was obtained by recrystallization from petroleum ether.

Workup

  1. additionwas added dropwise a solution
  2. customA precipitate formed upon addition
  3. filtrationwas then filtered
  4. washThe filtrate was washed with water (25 mL)
  5. customThe organic phase was removed
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in a rotary evaporator
  9. customAn analytical sample (m.p. 51°-54° C.) was obtained by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-e966fc34d3a44369b167b81fce16ce7d
Source dataset
uspto-grants-1994_02
Patent number
US05288871

Reaction notes

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