Catechol → Naphthalene

HRID 1190239Notes

Reaction equation

HRID 1190239 reaction equation
BrC1C=CC=CC=1[C:8]1[C:9]2[C:14]([C:15](C3C=CC=CC=3Br)=[C:16]3[C:21]=1C=CC=C3)=[CH:13][CH:12]=[CH:11][CH:10]=2.BrC1C2C(=CC=CC=2)C(C2C3C(=CC=CC=3)C(C3C4C(C(Br)=C5C=3C=CC=C5)=CC=CC=4)=CC=2)=C2C=1C=CC=C2.OC(C(O)(C)C)(C)C.C1(C(=CC=CC=1)O)O>>[CH:13]1[C:14]2[C:9](=[CH:8][CH:21]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 289CatecholHCID 6425PinacolHCID 57702611HCID 57702611, compoundHCID 59760676HCID 59760676, compound

Product 1

HCID 931Naphthalene

Procedure

Preparation analogous to Example 3b. Instead of 19.5 g (40 mmol) of 9,10-bis(2-bromophenyl)anthracene, 25.5 g (40 mmol) of 1,4-bis(10-bromoanthracen-9-yl)naphthalene are used, and instead of 10.6 g (90 mmol) of pinacol, 9.9 g (90 mmol) of pyrocatechol are used. Sublimation at p=1×10−5 mbar, T=330° C. Yield: 17.7 g (25 mmol), 61.8% of theory; purity: 99.7% according to 1H-NMR.

Workup

  1. customPreparation analogous to Example 3b
  2. customat p=1×10−5 mbar, T=330° C

Sources & evidence

ORD record
ord-bacc7fefea6a4017b27126e016d0778c
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Reaction notes

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