Sulfuric Acid → Methyl 3-hydroxy-4-(1-adamantyl)benzoate

HRID 1757470Notes

Reaction equation

HRID 1757470 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]12(O)[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.S(=O)(=O)(O)O>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 641521-AdamantanolHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 19387991Methyl 3-hydroxy-4-(1-adamantyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.16 g (80 mM) of methyl 3-hydroxybenzoate and 12.16 g (80 mM) of adamantanol in 160 ml of dichloromethane are treated with a dropwise addition of 4.37 ml of concentrated sulphuric acid. The reaction mixture is stirred at room temperature overnight. The solid residue is washed withwater and dried to lead to 18.3 g (79.9%) of the expected derivative, of melting point 244°-246° C.

Workup

  1. washThe solid residue is washed withwater and
  2. customdried

Sources & evidence

ORD record
ord-0f34cd992d774292aeede56607f141e7
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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