Ammonium formate → Methyl 3-cyclopentyloxy-4-hydroxybenzoate

HRID 1940318Notes

Reaction equation

HRID 1940318 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17]CC2C=CC=CC=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[OH:17])[C:10]([O:12][CH3:13])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21187943Methyl 3-cyclopentyloxy-4-benzyloxybenzoate

Product 1

HCID 21187838Methyl 3-cyclopentyloxy-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 3-cyclopentyloxy-4-benzyloxybenzoate (2.64 g; that is prepared as described in Reference Example 39) in methanol (120 mL) is treated with palladium on charcoal (5%,0.5 g) and ammonium formate (2.0 g) and heated at reflux for 45 minutes. The catalyst is filtered off through a pad of diatomaceous earth and washed with methanol. The flitrate and washings are evaporated under reduced pressure, and the resulting residue is subjected to flash chromatography on silica gel using a mixture of diethyl ether and pentane 1:1 v/v), to give methyl 3-cyclopentyloxy-4-hydroxybenzoate (1.8 g), in the form of a cream solid, m.p. 73°-75° C.

Workup

  1. customthat is prepared
  2. temperatureheated
  3. temperatureat reflux for 45 minutes
  4. filtrationThe catalyst is filtered off through a pad of diatomaceous earth
  5. washwashed with methanol
  6. customThe flitrate and washings are evaporated under reduced pressure
  7. additiona mixture of diethyl ether and pentane 1:1 v/v),

Sources & evidence

ORD record
ord-4b6d1cce2927425ea75e4d2a79b14366
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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