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

HRID 2412849Notes

Reaction equation

HRID 2412849 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

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.

Workup

  1. customThe resultant crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-007bb89e07bf4bfe9906e02a7addadbd
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

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