Water → Methyl 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoate

HRID 1903422Notes

Reaction equation

HRID 1903422 reaction equation
[OH:1][C:2]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]([CH3:37])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5].[C:38]1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[OH:1][C:2]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]([CH3:37])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:38])=[O:27])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 1282407121-(2-Hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoic acid

Product 1

HCID 12824097Methyl 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3 g of the above 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoic acid in 10 ml of methanol is added p-toluenesulfonic acid (30 mg), followed by heating under reflux for 2 hours. After cooling to room temperature, water is added and the mixture is stirred at 0° C. to give colorless crystals of methyl 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoate. m.p. 72°-72.5° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-f6c8c053b7e249c18e342c075fef6f40
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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