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

HRID 1437832노트

반응식

HRID 1437832 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-d0d4a35e015a466497e96d08160ba9d1
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622598B2

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