Hydrochloric Acid → 13-Oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

HRID 2412848Notes

Reaction equation

HRID 2412848 reaction equation
C([O:4][C:5]1[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21])=[C:9]([CH3:23])[CH:8]=[C:7]([O:24][CH3:25])[C:6]=1[O:26][CH3:27])(=O)C.[O:28]1CCN(C2CCCCCCCCCCC=2)CC1.Cl.C(OC1C(OC)=C(OC)C=C(C)C=1CCCCCCCCCC([CH:73]1[CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:79][CH2:78][CH2:77][CH2:76][CH2:75][C:74]1=[O:85])=O)(=O)C.[OH-].[Na+]>C(N(CC)CC)C>[O:21]=[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1[C:9]([CH3:23])=[CH:8][C:7]([O:24][CH3:25])=[C:6]([O:26][CH3:27])[C:5]=1[OH:4])[CH2:73][CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:79][CH2:78][CH2:77][CH2:76][CH2:75][C:74]([OH:85])=[O:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77315HCID 77315, compoundHCID 204311666-(9-Chloroformylnonyl)-2,3-dimethoxy-5-methylphenyl acetateHCID 20431171HCID 20431171, compound

Product 1

HCID 1337051013-Oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In the presence of triethylamine (14.3 ml), 6-(9-chloroformylnonyl)-2,3-dimethoxy-5-methylphenyl acetate (36.9 g) is reacted with 1-morpholino-1-cyclododecene (24.3 g) as in the corresponding step of Reference Example 5. The reaction product is treated with 6N--HCl (47 ml) and the resultant 2-[10-(2-acetoxy-3,4-dimethoxy-6-methylphenyl)decanoyl]cyclododecanone (46.3 g) is hydrolyzed with a 6N-aqueous solution of sodium hydroxide to obtain 32.4 g of 13-oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid, m.p. 63°-64° C.

Workup

  1. additionThe reaction product is treated with 6N

Sources & evidence

ORD record
ord-8fa3b4f7d60948a1b821e24d53e35903
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

Loading…