Methanol → 3-(Benzyloxy)-5-(cyclopentyloxy)benzoic acid

HRID 1990213Notes

Reaction equation

HRID 1990213 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=2)[C:10]([O:12]C)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].CO>C1COCC1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=2)[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 53629659Methyl 3-(cyclopentyloxy)-5-[(phenylmethyl)oxy]benzoate

Product 1

HCID 591271153-(Benzyloxy)-5-(cyclopentyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(cyclopentyloxy)-5-[(phenylmethyl)oxy]benzoate (9.25 g, 28.34 mmol) was dissolved in THF (120 mL) and a solution of lithium hydroxide mono hydrate (3.49 g, 85.0 mmol) in water (60 mL) added. The bi-phasic solution was stirred at RT for 16 hours (LCMS indicated reaction 80% complete), methanol (15 mL) added and the mixture stirred for a further 4 hours. The THF was removed in vacuo then water (40 mL) added and the pH adjusted to 7 with hydrochloric acid. The solid was collected and washed thoroughly with cold water (8.85 g).

Workup

  1. additionadded
  2. stirringthe mixture stirred for a further 4 hours
  3. customThe THF was removed in vacuo
  4. additionwater (40 mL) added
  5. customThe solid was collected
  6. washwashed thoroughly with cold water (8.85 g)

Sources & evidence

ORD record
ord-fddbe6aa4c154b699cd3c0a522ce3a76
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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