3-Chlorobenzoic Acid → HCID 12878380, compound

HRID 616982Notes

Reaction equation

HRID 616982 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]=[CH:9][CH2:8]2)(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(O)=[O:20].[OH-].[Na+]>ClCCl>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]1[O:20][CH:9]1[CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 54000274HCID 54000274, compound

Product 1

HCID 12878380HCID 12878380, compoundYield 116.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 15.12 g of 1,4-dihydro-6-naphthol acetate in 160 ml of dichloromethane is cooled to 0° C while 10.5 g of m-chlorobenzoic acid is added over 10 minutes. The mixture is stirred overnight at room temperature and then poured into a slurry of 100 g of ice and 50 ml of 10% aqueous sodium hydroxide. The layers are separated, the aqueous layer re-extracted with dichloromethane (two 100 ml portions), and the combined extracts are washed with water, dried, and evaporated in vacuo to give 16 g of the title compound as a yellow liquid.

Workup

  1. additionis added over 10 minutes
  2. customThe layers are separated
  3. extractionthe aqueous layer re-extracted with dichloromethane (two 100 ml portions)
  4. washthe combined extracts are washed with water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b9fa727844d43338b9dba1cb7faba1e
Source dataset
uspto-grants-1978_02
Patent number
US04076843

Reaction notes

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