Phenol → Phenyl Nonanoate

HRID 1600549Notes

Reaction equation

HRID 1600549 reaction equation
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].ClCC(Cl)=O.[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[C:1]([O:11][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 996PhenolHCID 6577Chloroacetyl chlorideHCID 8158Nonanoic Acid

Product 1

HCID 11075358Phenyl NonanoateYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5.00 g (31.6 mmol) of nonanoic acid, 3.93 g (34.76 mmol) of chloroacetyl chloride (CAC), 2.7 g (31.6 mmol) of phenol, and 35 ml of acetonitrile was delivered to a clean, dry, two neck 100 ml round bottom flash fitted with a mechanical stirrer and a reflux condenser. The reaction flask was flushed with nitrogen through a gas inlet at the top of the reflux condenser and placed in an 80° C. oil bath and stirred for 19 hours. The reaction mixtures was allowed to cool to room temperature and then vacuum filtered through 30 g of neutral alumina to remove chloroacetic acid. The purified product was then placed on a high vacuum line overnight to remove any residual solvent. Phenyl nonanoate (NOB) was isolated as a faint yellow liquid (6.18 g, 26.37 mmol) in 83% yield. The purity of NOB was determined to be over 97%.

Workup

  1. customdry
  2. customtwo neck 100 ml round bottom flash fitted with a mechanical stirrer and a reflux condenser
  3. customThe reaction flask was flushed with nitrogen through a gas inlet at the top of the reflux condenser
  4. customplaced in an 80° C.
  5. customThe reaction mixtures
  6. filtrationvacuum filtered through 30 g of neutral alumina
  7. customto remove chloroacetic acid
  8. customwas then placed on a high vacuum line overnight
  9. customto remove any residual solvent

Sources & evidence

ORD record
ord-b6895af1e34b4b3ea4d0e62422e815b8
Source dataset
uspto-grants-1999_11
Patent number
US05977044

Reaction notes

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