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

HRID 580983ノート

反応式

HRID 580983 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0e1d60b381e94d89986a15f04ab302e9
出典データセット
uspto-grants-1999_07
特許番号
US05919793

反応ノート

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