Methanol → Methyl 4-benzyloxy-2-ethyl-3-methylbenzoate

HRID 453406Notes

Reaction equation

HRID 453406 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH2:18][CH3:19])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:26]O>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:26])=[O:14])=[C:11]([CH2:18][CH3:19])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 668185814-Benzyloxy-2-ethyl-3-methylbenzoic acid

Product 1

HCID 67390959Methyl 4-benzyloxy-2-ethyl-3-methylbenzoate

Conditions

Temperature
67 °C

Procedure

19.7 g of 4-benzyloxy-2-ethyl-3-methylbenzoic acid (D1) are dissolved in 200 ml of methanol. 5.0 ml of H2SO4 (95-98%, extra pure) are subsequently added. The reaction solution is heated under reflux at 67° C. for 18 h overnight and subsequently evaporated to ⅓ of the volume in vacuo, and 200 ml of water are added. The mixture is then extracted twice with 200 ml of ethyl acetate each time. The combined organic phases are subsequently washed with saturated NaHCO3 solution, dried over Na2SO4 and evaporated in vacuo, giving 17.5 g of the title compound as a colourless oil; MS: 285.2 (MH+); TLC: Rf=0.72 (cyclohexane/methyl tert-butyl ether 1:1 parts by volume).

Workup

  1. temperatureThe reaction solution is heated
  2. customsubsequently evaporated
  3. additionare added
  4. extractionThe mixture is then extracted twice with 200 ml of ethyl acetate each time
  5. washThe combined organic phases are subsequently washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f6dce77ef40749b388043521320b0e62
Source dataset
uspto-grants-2013_07
Patent number
US08492440B2

Reaction notes

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