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

HRID 2425478Notes

Reaction equation

HRID 2425478 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]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(2S)-1-methoxypropan-2-yl]oxy-5-phenylmethoxy-benzoate (CAS no. 851885-42-2) (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-cdc345d5856742a1a94d5683c317d43c
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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