Ethanol → 6-Octyloxy-2-naphthoic acid

HRID 346080Notes

Reaction equation

HRID 346080 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[K+].C(O)C>O>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 81401-BromooctaneHCID 14797Potassium Hydroxide2×HCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 140083896-Octyloxy-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6-Hydroxynaphthalene-2-carboxylic acid (39.8 g), 1-bromooctane (61.3 g), potassium hydroxide (23.7 g), ethanol (900 ml) and water (120 ml) were stirred and refluxed for 16 hours. 10% Aqueous potassium hydroxide (200 ml) was added and refluxing was continued for a further 2 hours, when the solution was poured into water (5 liter) and acidified to ph 1. The solid was filtered, washed with water, dried and recrystallised from acetic acid to give the product (49.0 g, 77.2% theory) as a white crystalline solid, mpt 150°-153° C. (98.2% pure by hplc).

Workup

  1. temperaturerefluxed for 16 hours
  2. temperaturerefluxing
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallised from acetic acid
  7. customto give the product (49.0 g, 77.2% theory) as a white crystalline solid, mpt 150°-153° C. (98.2% pure by hplc)

Sources & evidence

ORD record
ord-0c60fc9c7d2d4369bc4e91d6229ef8fa
Source dataset
uspto-grants-1991_10
Patent number
US05061399

Reaction notes

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