1-Naphthol → HCID 20250613, compound

HRID 1284884Notes

Reaction equation

HRID 1284884 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:12](O)(=[O:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].B(F)(F)F.CCOCC>O>[C:12]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]=1[OH:11])(=[O:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8000Boron trifluoride etherateHCID 13849Pentadecanoic Acid

Product 1

HCID 20250613HCID 20250613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Naphthol (72.1 g, 500 mmol) and pentadecanoic acid (121.2 g, 500 mmol) were mixed with boron trifluoride etherate (400 ml) and heated on a steam bath for 4 hours. Then 400 ml water was carefully added and heating was continued to remove as much of the ether as possible. The precipitated solid was filtered off, washed well with water and air dried. The crude product was recrystallized from ethanol to give the pentadecanoylnaphthol as light yellow plates. Yield: 110 g (60 percent).

Workup

  1. temperatureheated on a steam bath for 4 hours
  2. temperatureheating
  3. customto remove as much of the ether as possible
  4. filtrationThe precipitated solid was filtered off
  5. washwashed well with water and air
  6. customdried
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-af7431f2b02e4538a304b3f41acb1288
Source dataset
uspto-grants-1986_01
Patent number
US04564577

Reaction notes

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