P-Cresol → Pentanoic acid, 4-methylphenyl ester

HRID 1636440Notes

Reaction equation

HRID 1636440 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([CH3:15])[CH:9]=1.C(N(CC)CC)C>ClCCl>[C:1]([O:14][C:13]1[CH:12]=[CH:11][C:10]([CH3:15])=[CH:9][CH:8]=1)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 2879P-CresolHCID 8471TriethylamineHCID 61186Valeryl chloride

Product 1

HCID 82613Pentanoic acid, 4-methylphenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pentanoyl chloride (39.8 g) in dichloromethane (50 ml) was added slowly to a solution of p-cresol (32.4 g) and triethylamine (36.4 g) in dichloromethane (250 ml) with ice cooling. After 1 hour the reaction mixture was washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 4-methylphenyl pentanoate.

Workup

  1. washAfter 1 hour the reaction mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-541e00b65b5d418abd6f7fd9509d2e77
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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