Methanol → Methyl 3-cyclopentyloxy-4-benzyloxybenzoate

HRID 1383518Notes

Reaction equation

HRID 1383518 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([OH:12])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:29]O>>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]([O:12][CH3:29])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 211879313-Cyclopentyloxy-4-benzyloxybenzoic acid

Product 1

HCID 21187943Methyl 3-cyclopentyloxy-4-benzyloxybenzoate

Procedure

A solution of 3-cyclopentyloxy-4-benzyloxybenzoic acid (5.1 g; that is prepared as described in Reference Example 38) in methanol (150 mL) and concentrated sulfuric acid (1 mL) is heated at reflux for 6 hours, and then it is cooled and concentrated in vacuo. The resulting residue is treated with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate solution (50 mL). The organic layer is collected, dried and evaporated. The resulting oil is subjected to flash chromatography on silica gel, using a mixture of ethyl acetate and pentane (1:4 v/v) as eluent, to give methyl 3-cyclopentyloxy-4-benzyloxybenzoate (4.8 g), in the form of a white solid, m.p. 58-59° C.

Workup

  1. customthat is prepared
  2. temperatureat reflux for 6 hours
  3. temperatureit is cooled
  4. concentrationconcentrated in vacuo
  5. additionThe resulting residue is treated with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  6. customThe organic layer is collected
  7. customdried
  8. customevaporated
  9. additiona mixture of ethyl acetate and pentane (1:4 v/v) as eluent

Sources & evidence

ORD record
ord-120f8a09594840d29fc89d3563492538
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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