p-Toluenesulfonic acid → 22-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

HRID 2412849ノート

反応式

HRID 2412849 の反応式
O=[C:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[C:31]([CH3:32])=[CH:30][C:29]([O:33][CH3:34])=[C:28]([O:35][CH3:36])[C:27]=1[OH:37])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C)C=O.S1(CCCC1)(=O)=O>C1CCCCC1>[OH:37][C:27]1[C:28]([O:35][CH3:36])=[C:29]([O:33][CH3:34])[CH:30]=[C:31]([CH3:32])[C:26]=1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 31347SulfolaneHCID 1337051013-Oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

生成物 1

HCID 1282407422-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid収率 58.6%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

実験手順

13-oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid (5.21 g) is reduced in the presence of p-toluenesulfonic acid (250 mg) and p-toluenesulfonyl hydrazide (2.33 g) in a solvent mixture of dimethylformamide (25 ml)-sulfolane (25 ml)-cyclohexane (25 ml) as in the corresponding step of Reference Example 5. The resultant crude product is recrystallized from methanol to obtain 2.97 g of 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid, m.p. 67° C.-68° C. The physico-chemical constants of this product are all in agreement with those of the crystals obtained in Reference Example 4.

後処理

  1. customThe resultant crude product is recrystallized from methanol

出典と根拠

ORDレコード
ord-007bb89e07bf4bfe9906e02a7addadbd
出典データセット
uspto-grants-1985_01
特許番号
US04495104

反応ノート

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