M-Cresol → Benzoic acid, 3-methylphenyl ester

HRID 1415889Notes

Reaction equation

HRID 1415889 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17].C(N(CC)CC)C>CCOCC>[C:1]([O:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:17])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 69193Benzoic acid, 3-methylphenyl esterYield 212%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of benzoyl chloride (32.5 g, Aldrich) in ether (200 ml) was added dropwise to a stirred solution of m-cresol (25.0 g, Aldrich) and triethylamine (27.2 g, Aldrich) in ether (500 ml). The reaction mixture was stirred at room temperature for 1 hour then filtered. The ethereal filtrate was washed with saturated NaHCO3 and water then dried over Na2SO4. The ether layer was separated, dried and concentrated in vacuo to give the desired product (104.0 g) as a white solid, mp 45-47C. 1H NMR consistent with the desired structure.

Workup

  1. filtrationthen filtered
  2. washThe ethereal filtrate was washed with saturated NaHCO3 and water
  3. dry with materialthen dried over Na2SO4
  4. customThe ether layer was separated
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8232430216cf41ae9ef7c1d6c1f2ebf5
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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