Sulfuric Acid → 2-(1-Adamantyl)-4-bromophenol

HRID 1491506Notes

Reaction equation

HRID 1491506 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[C:9]12(O)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:9]12([C:5]3[CH:4]=[C:3]([Br:8])[CH:2]=[CH:1][C:6]=3[OH:7])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 78084-BromophenolHCID 641521-AdamantanolHCID 516892Sodium Bicarbonate

Product 1

HCID 46704942-(1-Adamantyl)-4-bromophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

34.6 g (200 mmol) of p-bromophenol and 30.4 g (200 mmol) of 1-adamantanol are dissolved in 100 ml of dichloromethane. To the resulting solution there are slowly added 10 ml of concentrated sulfuric acid. The mixture is stirred for 8 hours at ambient temperature, poured into water, neutralized with sodium bicarbonate, extracted with methylene chloride, dried and evaporated. After recrystallization in isooctane 52.8 g of the expected product are obtained. Yield - 86%. Melting point: 140°-141° C.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. customevaporated
  4. customAfter recrystallization in isooctane 52.8 g of the expected product
  5. customare obtained
  6. customYield - 86%

Sources & evidence

ORD record
ord-cefe6fb9d92041498fbb5c411ae793ba
Source dataset
uspto-grants-1994_12
Patent number
USRE034805

Reaction notes

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