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

HRID 1165445

반응식

HRID 1165445 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8fd7d4478c3e4267980fcf98f96b7636
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910202

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