Dichloromethane → HCID 20074592, compound

HRID 614572Notes

Reaction equation

HRID 614572 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](C(O)=O)=[CH:4][CH:3]=1.C(Cl)Cl.[C:18](OC(=O)C)(=[O:20])[CH3:19].[C:25]([O:28]C(O)=O)(=[O:27])C>C(N(CC)CC)C.O1CCCC1>[C:18]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:25]([OH:28])=[O:27])[CH:3]=1)(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 3442911-Hydroxy-4-naphthoic acidHCID 17769302Acetoxy carboxylic acid

Product 1

HCID 20074592HCID 20074592, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 2.3 g. of 4-hydroxy-1-naphthoic acid in 100 ml. of methylene chloride and 100 ml. of tetrahydrofuran, a mixture of 1.5 g. of triethylamine, 1.6 g. of 4-N-dimethylaminopyridine and 1.5 g. of acetic anhydride is added. The reaction mixture is heated at 50° for one hour. The solution is extracted with ethyl acetate, the organic layer washed with water and dilute hydrochloride acid and evaporated to dryness to yield 2.1 g. of the acetoxy carboxylic acid.

Workup

  1. additionTo a suspension of 2.3 g
  2. temperatureThe reaction mixture is heated at 50° for one hour
  3. extractionThe solution is extracted with ethyl acetate
  4. washthe organic layer washed with water and dilute hydrochloride acid
  5. customevaporated to dryness
  6. customto yield 2.1 g

Sources & evidence

ORD record
ord-d13c83f37c464df289808309d006fe33
Source dataset
uspto-grants-1979_03
Patent number
US04145443

Reaction notes

Loading…