Hydrochloric Acid → HCID 642500, 화합물

HRID 1437834노트

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HRID 1437834 반응식
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[CH:13](=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O.O.[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:13]([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 642500HCID 642500, 화합물HCID 6093260Calcium chloride, dihydrateHCID 23689386Potassium hydroxide methanol

생성물 2

HCID 642500HCID 642500, 화합물수율 61%HCID 23134889HCID 23134889, 화합물수율 20%

실험 절차

5-Chloro-2,4-dihydroxy-6-methylbenzaldehyde (112 mg, 0.60 mmol) described in M. M. Joullie et al., J. Org. Chem., 50, 3997 (1985), dodecanal (133 mg, 0.72 mmol) and calcium chloride dihydrate (58 mg, 0.40 mmol) were stirred in a 0.4 M potassium hydroxide methanol solution (2 ml) at 0° C. for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid, extracted with ethyl acetate, and after post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1) to obtain 5-chloro-2,4-dihydroxy-6-methylbenzaldehyde (68 mg, recovery 61%) and 5-chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (45 mg, yield 20%).

후처리

  1. extractionextracted with ethyl acetate
  2. customafter post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1)

출처 및 근거

ORD 기록
ord-38a243b350184aa791e696345296b9ba
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622598B2

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