Benzyl Bromide → 4-Benzyloxy-2-ethyl-3-methylbenzoic acid

HRID 453409Notes

Reaction equation

HRID 453409 reaction equation
[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH2:1][CH3:2])[C:11]=1[CH3:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 227173732-Ethyl-4-hydroxy-3-methylbenzoic acid

Product 1

HCID 668185814-Benzyloxy-2-ethyl-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.10 g of 2-ethyl-4-hydroxy-3-methylbenzoic acid (E1) are dissolved in 50 ml of acetone. 3.30 ml of benzyl bromide and 5.10 g of K2CO3 are subsequently added. The reaction suspension is heated under reflux for 18 h overnight, subsequently filtered off with suction, and the filtrate obtained is evaporated to dryness in vacuo. The residue is dissolved in 40 ml of ethanol, and 40 ml of 2.0 N NaOH solution are added. The mixture is then heated under reflux for 3 h. The clear solution is diluted with 150 ml of water and adjusted to pH 1 using 20% hydrochloric acid. After stirring for 30 min, the precipitate formed is filtered off with suction, rinsed with water and dried at 90° C. in vacuo overnight, giving 2.45 g of the title compound as a beige, amorphous solid having a melting point of 169° C.; MS: 270.0 (M+); TLC: Rf=0.36 (cyclohexane/ethyl acetate 2:1 parts by volume).

Workup

  1. temperatureThe reaction suspension is heated
  2. temperatureunder reflux for 18 h overnight
  3. filtrationsubsequently filtered off with suction
  4. customthe filtrate obtained
  5. customis evaporated to dryness in vacuo
  6. dissolutionThe residue is dissolved in 40 ml of ethanol
  7. addition40 ml of 2.0 N NaOH solution are added
  8. temperatureThe mixture is then heated
  9. temperatureunder reflux for 3 h
  10. additionThe clear solution is diluted with 150 ml of water
  11. customthe precipitate formed
  12. filtrationis filtered off with suction
  13. washrinsed with water
  14. customdried at 90° C. in vacuo overnight

Sources & evidence

ORD record
ord-7c7295df93174aa9aa0c3f9b5fa44091
Source dataset
uspto-grants-2013_07
Patent number
US08492440B2

Reaction notes

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