1-Naphthol → 2-(4-Chlorobutyryl)-1-naphthol

HRID 1165023Notes

Reaction equation

HRID 1165023 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.[Cl:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17].B(F)(F)F.CCOCC>O>[Cl:12][CH2:13][CH2:14][CH2:15][C:16]([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:17]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8000Boron trifluoride etherateHCID 123004-Chlorobutanoic acid

Product 1

HCID 156179222-(4-Chlorobutyryl)-1-naphtholYield 38.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1-naphthol (15.14 g, 0.105 mole), 4-chlorobutyric acid (9.90 mL, 0.100 mole), and boron trifluoride etherate (75 mL) was heated on a steam bath for 4 hours. The mixture was then treated slowly with 100 mL of water, and heating continued for 30 minutes. The mixture was poured into water, stirred, and the solution decanted. The residue was triturated with water, then crystallized from ethanol to provide the title compound (9.50 g, 38%) as a pale green solid, mp 73°-79°.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. temperatureheating
  3. customthe solution decanted
  4. customThe residue was triturated with water
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-204f1209d0a949ed935a07ad133f133f
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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