Water → HCID 18974115, compound

HRID 2395031Notes

Reaction equation

HRID 2395031 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:19][CH2:20][CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[CH:11][C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ClC1C(=O)C(C#N)=C(C#N)C(=[O:40])C=1Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:29][CH:30]=2)=[CH:11][C:12]2[C:13](=[O:40])[CH2:14][CH2:15][CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 53765148HCID 53765148, compound

Product 1

HCID 18974115HCID 18974115, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-(3-benzyloxy-5,6,7,8-tetrahydro-2-naphthyl) propyl]benzoic acid (1.6 g) in ethyl acetate (50 ml) was added water (1 ml) and 2,3-dichloro-5,6-dicyanobenzoquinone (1.9 g). The mixture was stirred for 2 hours, the solvent evaporated and the residue subjected to chromatography on silica gel, eluting with 0.1% formic acid in EtOAc. The residue was purified by trituration with diethyl ether to give the title compound (0.3 g) mpt. 155°-160° C.

Workup

  1. customthe solvent evaporated
  2. washeluting with 0.1% formic acid in EtOAc
  3. customThe residue was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-1dfc408823694c278097263c274e90b2
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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