Benzaldehyde → 2-Hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehyde

HRID 1165445

反応式

HRID 1165445 の反応式
[CH:1](=[O:8])C1C=CC=CC=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([OH:21])[CH:14]=[CH:15][C:16]=1[C:17]([CH3:20])([CH3:19])[CH3:18].COC(Cl)Cl.Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[OH:21][C:13]1[CH:12]=[C:11]([O:10][CH3:9])[C:16]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:15][C:14]=1[CH:1]=[O:8]

参加物

7

反応物 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 122529764-Tert-butyl-3-methoxyphenol

生成物 1

HCID 198618272-Hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehyde収率 87%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

The benzaldehyde used in Example 6 was prepared as follows: (1) To a stirred solution of 2.91 g (16.14 mmol) of 3-methoxy-4-(1,1-dimethylethyl)phenol (see C. J. R. Adderley and F. R. Hewgill, J. Chem. Soc., (C), 1438, (1968) as an example of how to obtain this material) in 65 ml of methylene chloride and cooled in an ice-water bath was added 6.12 g (3.54 ml, 32.30 mmol) of titanium (IV) chloride followed by 3.06 g (2.41 ml, 26.64 mmol) of 1,1-dichlorodimethyl ether. The reaction mixture was stirred for 10 minutes and then poured into 16 ml of lN hydrochloric acid. The organic phase was separated, dried and evaporated. The residue was chromatographed on silica gel (146 g) using 1.5:98.5 (v/v) ether,hexane as eluent. There was obtained 2.92 g (14.01 mmol, 87%) of 2-hydroxy-4-methoxy-5-(1,1-dimethylethyl)benzaldehyde as a white solid after crystallization from pentane; mp 75°-78° C.

後処理

  1. customwas prepared
  2. temperaturecooled in an ice-water bath
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (146 g)

出典と根拠

ORDレコード
ord-8fd7d4478c3e4267980fcf98f96b7636
出典データセット
uspto-grants-1990_03
特許番号
US04910202

関連ノート

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