Tetrahydrofuran → 3-Benzyloxy-5-isopropoxybenzoic acid

HRID 1011679Notes

Reaction equation

HRID 1011679 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:8]([O:10]C)=[O:9])[CH3:3].C1COCC1.[OH-].[Na+]>CO>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:14]=1)[C:8]([OH:10])=[O:9])[CH3:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59127144Methyl 3-(benzyloxy)-5-isopropoxybenzoate

Product 1

HCID 534011033-Benzyloxy-5-isopropoxybenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[(1-methylethyl)oxy]-5-[(phenylmethyl)oxy]benzoate (37 g) in a 1:1 mixture of THF:methanol (300 mL) was added 4M sodium hydroxide solution (150 mL). The mixture was refluxed for 45 minutes, following which the organics were removed in vacuo. The aqueous was acidified to pH4 with hydrochloric acid (2M), and extracted with ethyl acetate. The organics were combined, washed with water and brine, dried (MgSO4) and concentrated in vacuo to give the desired compound (33.5 g), which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 45 minutes
  2. customorganics were removed in vacuo
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-759747e34f97471f8415488553b7ced6
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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