Sulfuric Acid → 3-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

HRID 618490

Reaction equation

HRID 618490 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[C:13]12(O)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.ClCCl.S(=O)(=O)(O)O>CCCCCCC>[C:13]12([C:6]3[C:7]([OH:12])=[CH:8][C:9]4[C:4]([CH:5]=3)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=4)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 271446-Bromo-2-naphthalenolHCID 641521-Adamantanol

Product 1

HCID 145490723-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

56 g (0.25 mol) of 6-bromo-2-naphthol, 38.2 g (0.25 mol) of 1-adamantanol and 500 ml of a mixture of dichloromethane and heptane (40/60) were introduced into a round-bottomed flask. 15 ml of concentrated sulfuric acid were added and the reaction mixture was stirred at room temperature for 48 hours. The solid was filtered off, washed with heptane (3×100 ml) and dissolved in ethyl ether and the organic phase was washed with water, separated by settling, dried over magnesium sulfate and evaporated. 60.1 g (67%) of the expected compound were collected, which compound had a melting point of 215°-6° C.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with heptane (3×100 ml)
  3. dissolutiondissolved in ethyl ether
  4. washthe organic phase was washed with water
  5. customseparated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. custom60.1 g (67%) of the expected compound were collected

Sources & evidence

ORD record
ord-be96ebb65c1343b38d103eb49bbac04f
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Linked notes

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