Hydrochloric Acid → 2,3-Dihydroxy-4-methoxybenzaldehyde

HRID 866045

反応式

HRID 866045 の反応式
[Na].[OH:2][C:3]1[C:10]([OH:11])=[C:9]([OH:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[OH-].[Na+].[CH3:15]OS(OC)(=O)=O.Cl>O>[OH:2][C:3]1[C:10]([OH:11])=[C:9]([O:12][CH3:15])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 750642,3,4-TrihydroxybenzaldehydeHCID 5360545Sodium

生成物 1

HCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde収率 72%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a vigorously stirred solution of sodium boratedecahydrate (borax, 30 g) in 600 mL of water was added 2,3,4-trihydroxy-benzaldehyde (5 g, 32.4 mmol). The yellow solution was stirred at room temperature for 30 min followed by dropwise and simultaneous addition (over 30 min) of sodium hydroxide (4.0 g, 100 mmol) in water (50 mL) and dimethylsulfate (9.45 mL, 100 mmol). Vigorous stirring was continued overnight and conc. hydrochloric acid was added to pH 1. After stirring for an additional 30 min the mixture was extracted with chloroform (5×300 ml). The organic layer was once washed with brine, dried and evaporated to yield a slightly yellowish solid which on crystallization from ethyl acetate-hexane afforded slightly yellowish colored needles (3.9 g, 72%), mp 116°-17° C.: (lit. 118°-119° C.), IR (film) 3374, 1646, 1505, 1461, 1443, 1278, 1210, 1106, 636 cm-1 ; 1H-NMR 3.987 (3H, s, OCH3), 5,466 (1H, brs, OH-3, D2O exchanged) 6.617 (1H, d, JAB =8.62, H-5), 7.147 (1H, d, JBA =8.62 HZ, H-6, 9,757 (1H, S, CHO) 11,113 (1H, brs, OH-2, D2O exchanged); and HREIMS (m/z, 168.0419 (M, 100%; calcd 168.0423 for C8H8O4).

後処理

  1. stirringVigorous stirring
  2. waitwas continued overnight
  3. stirringAfter stirring for an additional 30 min the mixture
  4. extractionwas extracted with chloroform (5×300 ml)
  5. washThe organic layer was once washed with brine
  6. customdried
  7. customevaporated
  8. customto yield a slightly yellowish solid which
  9. customon crystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-787a4ba535d54b0cb324f4242ed5dd46
出典データセット
uspto-grants-1996_10
特許番号
US05569786

関連ノート

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