Water → 2-Anthrol

HRID 414156Notes

Reaction equation

HRID 414156 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=1.CC(C)=O.C(=O)=O.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:16]=[CH:15][C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 115358102-methoxyanthraceneHCID 18522661Acetone cardice

Product 1

HCID 995032-Anthrol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2 g of 2-methoxyanthracene and 25 ml methylene chloride were stirred and chilled at -70° C. (acetone/dry-ice bath) under a dry atmosphere. A solution of 60 ml of methylene chloride and 11 ml of 1N boron tribromide in methylene chloride was added slowly through a compensating addition funnel. The mixture was then allowed to warm slowly to ambient temperature under a dry atmosphere. After 24 hours, 20 ml of water were added and the mixture was extracted with ether (4×25 ml). A brown solid, 1.7 g (92%), decomp. ca. 200° C. (lit.** decomp. 200° C.) was obtained after ether evaporation and drying under vacuum for 16 hours. IR (KBr): 3540-3460, 3460-3100 (--OH), 1630, 1480, 1460, 1410, 1380, 1320, 1280-1270, 1200-1170, 950, 880, 800, 735 cm-1. 1H NMR (CD3COCD3 /TMS): δ8.3, 8.44, 8.8; 8.13-7.8; 7.15-7.52 (ArH).

Workup

  1. extractionthe mixture was extracted with ether (4×25 ml)
  2. customca. 200° C. (lit.** decomp. 200° C.) was obtained
  3. customafter ether evaporation
  4. customdrying under vacuum for 16 hours

Sources & evidence

ORD record
ord-1b6a1611902c48149afe6b74b5e4d6c5
Source dataset
uspto-grants-1988_12
Patent number
US04790961

Reaction notes

Loading…