Hydrochloric Acid → 2,4-Dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde

HRID 1437832ノート

反応式

HRID 1437832 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5].[CH:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O.O.[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>>[OH:1][C:2]1[C:9]([CH:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 251690o-OrsellinaldehydeHCID 6093260Calcium chloride, dihydrateHCID 23689386Potassium hydroxide methanol

生成物 1

HCID 117720542,4-Dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde収率 28.7%

実験手順

2,4-Dihydroxy-6-methylbenzaldehyde (91 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 (59 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. After extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1) to obtain 2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (58 mg, yield 28%).

後処理

  1. customAfter extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-d0d4a35e015a466497e96d08160ba9d1
出典データセット
uspto-grants-2009_11
特許番号
US07622598B2

反応ノート

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