Lauric Acid → 1-(5-Chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone

HRID 1834534

Reaction equation

HRID 1834534 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].[C:13](O)(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:7]2[OH:12]

Participants

4

Reactant 2

HCID 3893Lauric AcidHCID 123363935-Chloronaphthalen-1-ol

Product 1

HCID 213252361-(5-Chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.6 parts of 5-chloro-1-naphthalenol [Erdmann and Kirchoff, Liebig's Ann., 247, 372 (1888)] 19.2 parts of dodecanoic acid and 132 parts of boron trifluoride ether complex (48% BF3) was stirred under nitrogen on a steam bath for 6 hours. Water (114 parts) was added and ether distilled off by further heating. The resulting mixture was cooled in ice and a tan solid was filtered and recrystallized from ethanol to give 18 parts of yellow 1-(5-chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone, m.p. 86°-87° C.

Workup

  1. distillationether distilled off by further heating
  2. temperatureThe resulting mixture was cooled in ice
  3. filtrationa tan solid was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6fc1b2102921450990b4db3de948ee41
Source dataset
uspto-grants-1978_01
Patent number
US04070481

Linked notes

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