Dichloromethane → HCID 13745631, compound

HRID 986703Notes

Reaction equation

HRID 986703 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Cl:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].C(N(CC)CC)C.ClCCl.[C:39](OC(=O)C)(=[O:41])[CH3:40]>CN(C)C1C=CN=CC=1.CO>[C:39]([O:28][C:5]1[C:6]([CH2:25][CH2:26][CH3:27])=[C:7]([CH:23]=[CH:24][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[Cl:22])(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 13338866HCID 13338866, compound

Product 1

HCID 13745631HCID 13745631, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-chlorobenzoic acid (1.0 g), which was prepared by the manner described in European Patent Application Publication No. 80,371, triethylamine (4.6 ml), 4-dimethylaminopyridine (8 mg) and dichloromethane (6 ml) was added acetic anhydride (3.1 ml) at 5° to 7° C., and the mixture was stirred well for 80 minutes. To the reaction mixture was added dropwise methanol (5 ml) to decompose the excess amount of acetic anhydride. The mixture was subjected to concentration, the residual oily product was poured into ice-water, and the precipitate was collected by filtration. Recrystallization from ethanol-water gave white crystals of 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-chlorobenzoic acid 975 mg). M.p. 146°-148° C.

Workup

  1. concentrationThe mixture was subjected to concentration
  2. additionthe residual oily product was poured into ice-water
  3. filtrationthe precipitate was collected by filtration
  4. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-286c438efab743db8b6d6e8518571a14
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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