1-Bromooctadecane → 3-Hydroxy-5-(octadecyloxy)benzoic acid methyl ester

HRID 1110280Notes

Reaction equation

HRID 1110280 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([O:1][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[CH:11]=[C:10]([OH:12])[CH:9]=1

Participants

6

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 152334783-Hydroxy-5-(octadecyloxy)benzoic acid methyl esterYield 32.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 50.0 g (0.297 mol) of methyl 3,5-dihydroxybenzoate, 99.2 g (0.297 mol) of 1-bromooctadecane and 41 g (0.297 mol) of potassium carbonate in 100 ml of acetone and 50 ml of DMF was stirred at reflux under argon for 24 hours. The solvents were removed at reduced pressure and the residue was heated with methylene chloride and filtered hot. The filtrate was concentrated at reduced pressure to a solid which was recrystallized from methylene chloride-methanol to give the 3,5-dialkylated product. The filtrate was concentrated to dryness and the residue was recrystallized from methylene chloride-methanol to give more of the dialkylated product. The filtrate was concentrated to dryness and recrystallized from ether-hexane to give 40.2 g (32% yield, mp 95°-97°) of 3-hydroxy-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureat reflux under argon for 24 hours
  2. customThe solvents were removed at reduced pressure
  3. temperaturethe residue was heated with methylene chloride
  4. filtrationfiltered hot
  5. concentrationThe filtrate was concentrated at reduced pressure to a solid which
  6. customwas recrystallized from methylene chloride-methanol
  7. customto give the 3,5-dialkylated product
  8. concentrationThe filtrate was concentrated to dryness
  9. customthe residue was recrystallized from methylene chloride-methanol
  10. customto give more of the dialkylated product
  11. concentrationThe filtrate was concentrated to dryness
  12. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-b030237d87a74d9d983abd11c76f7601
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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