Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate → methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

HRID 1175896Notes

Reaction equation

HRID 1175896 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17]CC2C=CC=CC=2)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])[CH3:5]>C1COCC1>[OH:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([O:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 1

HCID 59127167Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

Product 1

HCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoateYield 100,497.398%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[phenylmethyl]oxy}benzoate (50.0 g, 0.152 mmol) was dissolved in a mixture of THF:ethanol (600 mL) and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (5.0 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 20 hours until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, and the filtrate concentrated in vacuo to give the desired compound (36.7 g).

Workup

  1. customethanol (600 mL) and the flask evacuated
  2. custompurged with nitrogen (3 times)
  3. addition10% Palladium on carbon (5.0 g) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off
  9. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-59cf3d958d8648a9af932dbda2c0470f
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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