4-Methoxybenzoic Acid → Diisopropyl Ether

HRID 982246Notes

Reaction equation

HRID 982246 reaction equation
[OH:1][CH:2]([CH2:21][OH:22])[CH:3]([NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:23][CH:24]([CH2:44]O)[CH:25](NC(C1NC2C(C=1)=CC=CC=2)=O)C1C=CC=CC=1.COC1C=CC(C(O)=O)=CC=1.C(Cl)(=O)C(Cl)=O.NC(C1C=CC=CC=1)C(O)CO>C(N(CC)CC)C>[CH:2]([O:23][CH:24]([CH3:25])[CH3:44])([CH3:21])[CH3:3].[OH:1][CH:2]([CH2:21][OH:22])[CH:3]([NH:10][C:11](=[O:20])[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 74784-Methoxybenzoic AcidHCID 65578Oxalyl chlorideHCID 12701376HCID 12701376, compoundHCID 14650571HCID 14650571, compoundHCID 14650580HCID 14650580, compound

Product 2

HCID 7914Diisopropyl EtherHCID 14650580HCID 14650580, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-[(1RS, 2RS)-2,3-Dihydroxy-1-phenylpropyl]-4-methoxybenzamide may be prepared in the following manner: working as in Example 8 for the preparation of N-[(1RS, 2RS)-2,3-dihydroxy-1-phenylpropyl]-2-indolecarboxamide, but starting with 4-methoxybenzoic acid (3.7 g), oxalyl dichloride (2.26 cc), (2RS, 3RS)-3-amino-3-phenyl-1,2-propanediol (3.7 g) and triethylamine (9.26 cc) and after the precipitate is washed with distilled water and then with diisopropyl ether, N-[(1RS, 2RS)-2,3dihydroxy-1-phenylpropyl]-4-methoxybenzamide (5.5 g), m.p. 178° C., is obtained.

Workup

  1. washafter the precipitate is washed with distilled water

Sources & evidence

ORD record
ord-6a32ecaea5184c808e6eca0e4f6c9f03
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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