Ethanol → 1,3-Benzodioxole-5-carboxylic acid, 6-methoxy-

HRID 1598984Notes

Reaction equation

HRID 1598984 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:12]([O:14]C)=[O:13])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1.[OH-].[Na+].C(O)C>O>[CH3:1][O:2][C:3]1[C:4]([C:12]([OH:14])=[O:13])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18931116Methyl 6-Methoxybenzo[d][1,3]dioxole-5-carboxylate

Product 1

HCID 110525521,3-Benzodioxole-5-carboxylic acid, 6-methoxy-Yield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 6-methoxy-1,3-benzodioxole-5-carboxylate (3 g, 14 mmol), prepared as in Example 1, 20% sodium hydroxide (50 mL) and ethanol (25 mL) was heated 1 hour at reflux and then diluted with water, washed with diethyl ether (2×), treated with concentrated hydrochloric acid and cooled in an ice-bath. The solids were collected, washed with water (2×) and dried under vacuum at 70° C. to give 6-methoxy-1,3-benzodioxole-5-carboxylic acid (2.3 g, 12 mmol), m.p. 151° C.

Workup

  1. temperaturewas heated 1 hour
  2. temperatureat reflux
  3. washwashed with diethyl ether (2×)
  4. additiontreated with concentrated hydrochloric acid
  5. temperaturecooled in an ice-bath
  6. customThe solids were collected
  7. washwashed with water (2×)
  8. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-f94280474b7f4fe2a10aff68aa6ba646
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

Loading…