Methanol → 1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid

HRID 2075484Notes

Reaction equation

HRID 2075484 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH2:16][CH:17]1[O:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[O:19][CH2:18]1)=[O:4].[OH-].[Na+].CO>C1COCC1>[O:22]1[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[O:19][CH2:18][CH:17]1[CH2:16][O:15][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 667012071-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 231327931-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acidYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.31 g of 1-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester in 95 ml of THF were added 5.62 ml of 2 M aqueous sodium hydroxide and 30 ml of methanol. After 1 h at reflux and 16 h at room temperature the organic solvents were removed in vacuo. The residue was treated with 2 M hydrochloric acid, and three times extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, and concentrated and dried in vacuo to yield 0.94 g of 1-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid.

Workup

  1. customwere removed in vacuo
  2. additionThe residue was treated with 2 M hydrochloric acid, and three times
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-52fe8cd8dd0245649c71d6a50051d70e
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…