Hydrochloric Acid → 2-Hydroxy-5-(2-methoxyethoxy)benzoic acid

HRID 580983Notes

Reaction equation

HRID 580983 reaction equation
Cl([O-])=O.[Na+].[OH:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:10][C:7]=1[CH:8]=[O:9].C[O-:20].[Na+].Cl>CO.CS(C)=O.O>[OH:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:10][C:7]=1[C:8]([OH:20])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 23668197Sodium ChloriteHCID 537546562-Hydroxy-5-(2-methoxyethoxy)benzaldehyde

Product 1

HCID 537147262-Hydroxy-5-(2-methoxyethoxy)benzoic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium chlorite (8.08 g) was added over a period of 30 seconds to a stirred solution 2-hydroxy-5-(2-methoxyethoxy)benzaldehyde (see Example 41) and sodium methoxide in methanol (25% by weight solution, 9.68 ml) in dimethylsulphoxide (350 ml) at 15° C. After warming to room temperature and stirring for 3 hours the mixture was added to water (600 mls), acidified with 2M aqueous hydrochloric acid, and extracted with diethyl ether (4×250 mls). The ethereal extracts were combined, washed with water (2×100 ml), dried (MgSO4) and evaporated. The residue was crystallised from toluene to give 2-hydroxy-5-(2-methoxyethoxy)benzoic acid (4.1 g) as solid m.p. 115-116° C.; NMR 3.3(3H,s), 3.65(2H,m), 4.05(2H,m), 6.9(1H,d), 7.15(1H, d of d), 7.25(1H,d); m/z 213(M+H).

Workup

  1. extractionextracted with diethyl ether (4×250 mls)
  2. washwashed with water (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was crystallised from toluene

Sources & evidence

ORD record
ord-0e1d60b381e94d89986a15f04ab302e9
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

Loading…