Sulfamic Acid → 3-Cyclopentyloxy-4-benzyloxybenzoic acid

HRID 1940316Notes

Reaction equation

HRID 1940316 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)([OH:25])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:18]1([O:17][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13]([OH:25])=[O:14])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 5987Sulfamic Acid2×HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehydeHCID 23668197Sodium Chlorite2×

Product 1

HCID 211879313-Cyclopentyloxy-4-benzyloxybenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A rapidly stirred solution of 4-benzyloxy-3-cyclopentyloxybenzaldehyde (10.5 g; that is prepared as described in Reference Example 37) in glacial acetic acid (100 mL) is treated with sulfamic acid (4.85 g) and stirred at room temperature for 10 minutes. The solution is then cooled in an ice bath and treated with a solution of sodium chlorite (4.2 g) in water (100 mL) during 15 minutes at 13°-15° C. During the addition a white precipitate forms and, because stirring becomes difficult, a further quantity of glacial acetic acid (60 mL) is added. After warming to room temperature, the solution is stirred for a further 6 hours and further quantities of sodium chlorite (1.6 g) and sulfamic acid (1.7 g) are added. The mixture is poured onto water and the resulting solid is filtered off and dried, to give 3-cyclopentyloxy-4-benzyloxybenzoic acid (10 g).

Workup

  1. customthat is prepared
  2. temperatureThe solution is then cooled in an ice bath
  3. additionDuring the addition a white precipitate forms
  4. stirringbecause stirring
  5. temperatureAfter warming to room temperature
  6. stirringthe solution is stirred for a further 6 hours
  7. additionThe mixture is poured onto water
  8. filtrationthe resulting solid is filtered off
  9. customdried

Sources & evidence

ORD record
ord-a1622e98e31c4cbda6a7c68d028f66fd
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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