Acetic Acid → 2-(2,4-Dihydroxyphenyl)-2-methyl-heptane

HRID 1904030Notes

Reaction equation

HRID 1904030 reaction equation
C(O)(=O)C.S(=O)(=O)(O)O.[C:10]1([CH:17]=[CH:16][CH:15]=[C:13]([OH:14])[CH:12]=1)[OH:11].O[C:19]([CH3:26])([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:20]>O>[OH:11][C:10]1[CH:12]=[C:13]([OH:14])[CH:15]=[CH:16][C:17]=1[C:19]([CH3:26])([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 5054ResorcinolHCID 122422-Methyl-2-heptanol

Product 1

HCID 204660772-(2,4-Dihydroxyphenyl)-2-methyl-heptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 parts of glacial acetic acid containing 9.8 parts of 98% sulphuric acid was added 22 parts of resorcinol followed by 13 parts of 2-hydroxy-2-methyl-heptane at room temperature. After storing overnight at the same temperature the reaction mixture was poured into 1000 parts of water. The organic phase which separated out, was after decanting off the water, taken up in ether, washed with sodium bicarbonate solution, and finally with water. The ether solution was then evaporated and the residue distilled to give 2-(2,4-dihydroxyphenyl)-2-methyl-heptane (compound of the formula (4)) with a boiling point (b.p.12) of from 202°-204° C. and with the following percentage composition by weight:

Workup

  1. customThe organic phase which separated out
  2. customafter decanting off the water
  3. washwashed with sodium bicarbonate solution
  4. customThe ether solution was then evaporated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-4d9d9cf5a3f94ff6ba55704b13268e60
Source dataset
uspto-grants-1984_03
Patent number
US04439518

Reaction notes

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